Methyl (2′S,3′S)-3,4-O-(2′,3′-dimethoxy­butane-2′,3′-di­yl)-α-l-rhamnopyran­oside: a glycosyl acceptor

Tsai, Y.-F.; Yang, J.-T.; Chen, J.-D.; Lin, C.-H.

doi:10.1107/S1600536808008222

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 5| May 2008| Page o897

doi:10.1107/S1600536808008222

Open

access

Methyl (2′S,3′S)-3,4-O-(2′,3′-dimethoxybutane-2′,3′-diyl)-α-L-rhamnopyranoside: a glycosyl acceptor

Yow-Fu Tsai,^a ^* Jen-Ta Yang,^a Jhy-Der Chen ^a and Chia-Her Lin ^a

^aDepartment of Chemistry, Chung-Yuan Christian University, Chung-Li 320, Taiwan
^*Correspondence e-mail: tsaiyofu@cycu.edu.tw

(Received 11 March 2008; accepted 26 March 2008; online 23 April 2008)

The title compound, C₁₃H₂₄O₇, is the product of the ketalization of methyl L-(+)-rhamnopyranoside with 2,3-butanedione. It crystallizes with two molecules in the asymmetric unit, which are connected by O—H⋯O hydrogen bonds. The C-3,4 diequatorial hydroxy groups of the methyl L-(+)-rhamnopyranoside were protected, leaving the C-2 hydroxy group free. The L-(+)-rhamnopyranoside and 2′,3′-dimethoxybutane-2′,3′-diyl rings adopt chair conformations and all methoxy groups are in axial positions. The absolute configuration was assumed from the synthesis.

Related literature

For related literature, see: Duynstee et al. (1998 ); Lang & Wullbrandt (1999 ); Leisinger & Margraff (1979 ); Montchamp et al. (1996 ); Bauer et al. (2006 ).

Experimental

Crystal data

C₁₃H₂₄O₇
M_r = 292.32
Orthorhombic, P 2₁ 2₁ 2₁
a = 12.8743 (14) Å
b = 13.1182 (12) Å
c = 18.208 (3) Å
V = 3075.0 (7) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 295 (2) K
0.6 × 0.5 × 0.4 mm

Data collection

Bruker P4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.933, T_max = 0.994
3842 measured reflections
3032 independent reflections
2630 reflections with I > 2s(I)
R_int = 0.020
3 standard reflections every 97 reflections intensity decay: none

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.106
S = 1.01
3032 reflections
362 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5A⋯O13ⁱ	0.82	2.17	2.907 (3)	150
O12—H12A⋯O5ⁱⁱ	0.82	2.10	2.846 (3)	152
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) x, y-1, z.

Data collection: XSCANS (Siemens, 1995 ); cell refinement: XSCANS; data reduction: SHELXTL (Sheldrick, 2008 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablock I. DOI: 10.1107/S1600536808008222/bt2683sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808008222/bt2683Isup2.hkl

checkCIF report

Comment top

L-Rhamnopyranse-containing glycolipids display a wide range of biological properties (Leisinger, & Margraff, 1979; Lang & Wullbrandt, 1999; Bauer et al., 2006). For the above reason, we were interesting to study on the total synthesis of rhamnolipids. The title compound, C₁₃H₂₄O₇, which was synthesized by the ketalization of C-3,4 hydroxyl group of the methyl L-(+)-rhamnopyranoside, with 2,3-butanedione and chemoselectively protected the C-3,4 diequatorial hydroxyl group (Montchamp et al., 1996; Duynstee et al., 1998), was utilized as glycosyl acceptor in our synthetic strategy. The methyl L-(+)-rhamnopyranoside was prepared by acetalization of the commercial optical pure L-(+)-rhamnopyranose as starting material with methanol. The structure of L-rhamnopyranoside ring and 2',3'-dimethoxybutan-2',3'-diyl ring are chair conformation and all of methoxy groups are at axial position.

Related literature top

For related literature, see: Duynstee et al. (1998); Lang & Wullbrandt (1999); Leisinger & Margraff (1979); Montchamp et al. (1996); Bauer et al. (2006).

Experimental top

A solution of methyl L-(+)-rhamnopyranose ([a]²⁰_D = + 8.2°) (638 mg, 3.58 mmol), trimeyhyl orthoformate (1.20 ml, 10.75 mmol) and 2,3-butanedione (0.35 ml, 3.98 mmol) in dried methanol (15 ml) was treated with camphersulfonic acid (50 mg, 0.22 mmol). The mixture was refluxed for 18 h. The cool reaction mixture was then treated with NEt₃ and concentrated under reduced pressure to observe crude product. The crude product was purified via flash column chromatography on silica gel (EtOAc/n-hexane = 1:1) to obtain 874 mg (84%) of the title compound as white powder. The pure product was recrystalized from CH₂Cl₂ at room temperature.

Computing details top

Data collection: XSCANS (Siemens, 1995); cell refinement: XSCANS (Siemens, 1995); data reduction: SHELXTL (Sheldrick, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound, showing the atom numbering scheme. Displacement ellipsoids for non-H atoms are represented at the 30% probability level. The H atoms are drawn with an arbitrary radius.

Methyl (2'S,3'S)-3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-α-L-rhamnopyranoside top

Crystal data top

C₁₃H₂₄O₇	F(000) = 1264
M_r = 292.32	D_x = 1.263 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 27 reflections
a = 12.8743 (14) Å	θ = 5.1–12.5°
b = 13.1182 (12) Å	µ = 0.10 mm⁻¹
c = 18.208 (3) Å	T = 295 K
V = 3075.0 (7) Å³	Block, colourless
Z = 8	0.6 × 0.5 × 0.4 mm

Data collection top

Bruker P4 diffractometer	2630 reflections with I > 2s(I)
Radiation source: fine-focus sealed tube	R_int = 0.020
Graphite monochromator	θ_max = 25.0°, θ_min = 1.9°
ω scans	h = −1→15
Absorption correction: ψ scan (North et al., 1968)	k = −1→15
T_min = 0.933, T_max = 0.994	l = −1→21
3842 measured reflections	3 standard reflections every 97 reflections
3032 independent reflections	intensity decay: none

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.038	H-atom parameters constrained
wR(F²) = 0.106	w = 1/[σ²(F_o²) + (0.0561P)² + 0.7995P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
3032 reflections	Δρ_max = 0.15 e Å⁻³
362 parameters	Δρ_min = −0.17 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0063 (6)

Crystal data top

C₁₃H₂₄O₇	V = 3075.0 (7) Å³
M_r = 292.32	Z = 8
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 12.8743 (14) Å	µ = 0.10 mm⁻¹
b = 13.1182 (12) Å	T = 295 K
c = 18.208 (3) Å	0.6 × 0.5 × 0.4 mm

Data collection top

Bruker P4 diffractometer	2630 reflections with I > 2s(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.020
T_min = 0.933, T_max = 0.994	3 standard reflections every 97 reflections
3842 measured reflections	intensity decay: none
3032 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.106	H-atom parameters constrained
S = 1.02	Δρ_max = 0.15 e Å⁻³
3032 reflections	Δρ_min = −0.17 e Å⁻³
362 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.29481 (18)	0.87985 (15)	0.88054 (10)	0.0505 (5)
O2	0.1553 (2)	0.8215 (2)	0.95033 (13)	0.0673 (7)
O3	0.35887 (18)	0.66974 (18)	0.87880 (14)	0.0614 (6)
O4	0.20071 (17)	0.70426 (15)	0.82239 (11)	0.0469 (5)
O5	0.38039 (16)	0.96048 (16)	0.74810 (11)	0.0502 (5)
H5A	0.4138	0.9481	0.7854	0.075*
O6	0.11031 (18)	0.99268 (18)	0.71133 (13)	0.0626 (6)
O7	0.21798 (18)	0.86713 (17)	0.66048 (11)	0.0529 (5)
O8	0.38389 (15)	0.21315 (15)	0.83116 (10)	0.0426 (4)
O9	0.38270 (19)	0.33878 (17)	0.92121 (12)	0.0564 (6)
O10	0.17861 (17)	0.16879 (17)	0.87757 (12)	0.0548 (5)
O11	0.20194 (17)	0.33159 (15)	0.82917 (10)	0.0470 (5)
O12	0.37676 (17)	0.15454 (15)	0.67829 (11)	0.0481 (5)
H12A	0.3881	0.1110	0.7096	0.072*
O13	0.43863 (16)	0.41769 (15)	0.66158 (12)	0.0515 (5)
O14	0.27898 (16)	0.34098 (16)	0.63634 (10)	0.0451 (5)
C1	0.2596 (3)	0.8024 (3)	0.92943 (17)	0.0570 (9)
C2	0.3345 (4)	0.8045 (3)	0.99348 (19)	0.0829 (13)
H2A	0.3352	0.8714	1.0148	0.124*
H2B	0.4030	0.7875	0.9766	0.124*
H2C	0.3129	0.7558	1.0298	0.124*
C3	0.1350 (4)	0.9160 (3)	0.9869 (2)	0.0932 (15)
H3A	0.0622	0.9210	0.9977	0.140*
H3B	0.1551	0.9716	0.9557	0.140*
H3C	0.1740	0.9188	1.0317	0.140*
C4	0.2534 (3)	0.6969 (2)	0.89081 (17)	0.0507 (8)
C5	0.3743 (3)	0.5765 (3)	0.8392 (3)	0.0899 (15)
H5B	0.4473	0.5641	0.8335	0.135*
H5C	0.3425	0.5817	0.7916	0.135*
H5D	0.3433	0.5211	0.8659	0.135*
C6	0.1952 (3)	0.6187 (3)	0.9353 (2)	0.0671 (10)
H6A	0.1933	0.5553	0.9089	0.101*
H6B	0.1256	0.6420	0.9438	0.101*
H6C	0.2297	0.6088	0.9815	0.101*
C7	0.2429 (2)	0.7820 (2)	0.77618 (15)	0.0426 (7)
H7A	0.3160	0.7670	0.7659	0.051*
C8	0.2344 (2)	0.8829 (2)	0.81437 (15)	0.0436 (7)
H8A	0.1615	0.8952	0.8271	0.052*
C9	0.2721 (2)	0.9686 (2)	0.76624 (16)	0.0438 (7)
H9A	0.2589	1.0340	0.7904	0.053*
C10	0.2127 (3)	0.9639 (2)	0.69401 (17)	0.0497 (7)
H10A	0.2420	1.0145	0.6603	0.060*
C11	0.0474 (3)	1.0130 (4)	0.6492 (3)	0.1003 (16)
H11A	−0.0209	1.0325	0.6651	0.150*
H11B	0.0428	0.9529	0.6193	0.150*
H11C	0.0776	1.0674	0.6211	0.150*
C12	0.1820 (3)	0.7835 (2)	0.70469 (16)	0.0477 (7)
H12B	0.1080	0.7924	0.7154	0.057*
C13	0.1975 (3)	0.6876 (3)	0.6604 (2)	0.0698 (10)
H13A	0.1575	0.6917	0.6160	0.105*
H13B	0.1751	0.6298	0.6886	0.105*
H13C	0.2697	0.6802	0.6484	0.105*
C14	0.3400 (3)	0.2447 (2)	0.89914 (15)	0.0445 (7)
C15	0.3620 (3)	0.1598 (3)	0.95361 (17)	0.0591 (9)
H15A	0.4356	0.1497	0.9575	0.089*
H15B	0.3297	0.0980	0.9370	0.089*
H15C	0.3345	0.1780	1.0008	0.089*
C16	0.4938 (3)	0.3455 (3)	0.9215 (2)	0.0743 (11)
H16A	0.5144	0.4122	0.9375	0.111*
H16B	0.5197	0.3335	0.8728	0.111*
H16C	0.5216	0.2952	0.9544	0.111*
C17	0.2219 (3)	0.2663 (2)	0.89001 (16)	0.0471 (7)
C18	0.0701 (3)	0.1652 (3)	0.8604 (2)	0.0737 (11)
H18A	0.0493	0.0956	0.8532	0.111*
H18B	0.0574	0.2032	0.8162	0.111*
H18C	0.0310	0.1943	0.9000	0.111*
C19	0.1755 (3)	0.3204 (3)	0.95614 (18)	0.0642 (10)
H19A	0.1028	0.3319	0.9479	0.096*
H19B	0.2099	0.3845	0.9632	0.096*
H19C	0.1844	0.2788	0.9991	0.096*
C20	0.2480 (2)	0.2952 (2)	0.76220 (15)	0.0400 (6)
H20A	0.2181	0.2290	0.7489	0.048*
C21	0.3632 (2)	0.2850 (2)	0.77310 (14)	0.0388 (6)
H21A	0.3917	0.3515	0.7869	0.047*
C22	0.4147 (2)	0.2498 (2)	0.70284 (15)	0.0400 (6)
H22A	0.4902	0.2467	0.7094	0.048*
C23	0.3874 (2)	0.3265 (2)	0.64348 (15)	0.0425 (6)
H23A	0.4147	0.3017	0.5965	0.051*
C24	0.4307 (3)	0.4943 (3)	0.6062 (2)	0.0701 (10)
H24A	0.4665	0.5546	0.6222	0.105*
H24B	0.3589	0.5101	0.5978	0.105*
H24C	0.4615	0.4699	0.5616	0.105*
C25	0.2258 (2)	0.3727 (2)	0.70230 (15)	0.0430 (7)
H25A	0.2511	0.4399	0.7175	0.052*
C26	0.1112 (3)	0.3797 (3)	0.6822 (2)	0.0652 (10)
H26A	0.1019	0.4304	0.6447	0.098*
H26B	0.0718	0.3984	0.7249	0.098*
H26C	0.0877	0.3149	0.6643	0.098*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0683 (14)	0.0485 (11)	0.0347 (10)	−0.0162 (11)	−0.0075 (10)	0.0047 (9)
O2	0.0860 (18)	0.0663 (15)	0.0495 (12)	−0.0112 (14)	0.0156 (12)	−0.0026 (12)
O3	0.0551 (14)	0.0524 (12)	0.0768 (15)	−0.0051 (11)	−0.0090 (12)	0.0158 (12)
O4	0.0527 (12)	0.0444 (10)	0.0436 (10)	−0.0123 (10)	−0.0050 (10)	0.0060 (9)
O5	0.0487 (12)	0.0539 (12)	0.0480 (11)	−0.0057 (10)	−0.0044 (10)	0.0100 (10)
O6	0.0520 (13)	0.0695 (15)	0.0662 (14)	0.0071 (12)	−0.0070 (12)	0.0189 (12)
O7	0.0619 (13)	0.0616 (13)	0.0353 (10)	−0.0092 (11)	−0.0043 (10)	0.0041 (10)
O8	0.0487 (11)	0.0449 (10)	0.0341 (9)	0.0091 (9)	−0.0015 (9)	0.0017 (9)
O9	0.0694 (15)	0.0526 (12)	0.0473 (11)	0.0022 (12)	−0.0088 (11)	−0.0066 (11)
O10	0.0536 (12)	0.0520 (12)	0.0587 (13)	0.0000 (11)	0.0034 (11)	0.0075 (11)
O11	0.0538 (12)	0.0503 (11)	0.0368 (9)	0.0139 (10)	0.0053 (9)	0.0036 (9)
O12	0.0582 (12)	0.0424 (10)	0.0436 (10)	−0.0060 (10)	0.0036 (10)	−0.0028 (9)
O13	0.0543 (12)	0.0473 (11)	0.0530 (12)	−0.0147 (10)	−0.0035 (11)	0.0055 (10)
O14	0.0481 (12)	0.0549 (12)	0.0323 (9)	−0.0046 (10)	−0.0023 (8)	0.0026 (9)
C1	0.071 (2)	0.062 (2)	0.0384 (15)	−0.0189 (18)	−0.0021 (16)	0.0082 (14)
C2	0.119 (3)	0.086 (3)	0.0434 (18)	−0.035 (3)	−0.025 (2)	0.0195 (19)
C3	0.131 (4)	0.087 (3)	0.062 (2)	−0.003 (3)	0.024 (3)	−0.012 (2)
C4	0.0558 (19)	0.0491 (17)	0.0472 (16)	−0.0094 (15)	−0.0059 (15)	0.0139 (14)
C5	0.069 (2)	0.0473 (19)	0.154 (5)	0.0036 (19)	0.001 (3)	0.009 (3)
C6	0.077 (2)	0.063 (2)	0.062 (2)	−0.025 (2)	−0.009 (2)	0.0213 (17)
C7	0.0476 (16)	0.0417 (14)	0.0384 (14)	−0.0063 (13)	−0.0001 (13)	0.0035 (13)
C8	0.0511 (17)	0.0457 (15)	0.0342 (14)	−0.0060 (13)	−0.0045 (13)	0.0027 (13)
C9	0.0492 (16)	0.0419 (15)	0.0401 (15)	−0.0013 (13)	−0.0001 (13)	0.0040 (12)
C10	0.0528 (18)	0.0503 (17)	0.0460 (16)	−0.0033 (15)	−0.0022 (15)	0.0133 (14)
C11	0.066 (3)	0.142 (4)	0.093 (3)	0.003 (3)	−0.024 (2)	0.051 (3)
C12	0.0505 (17)	0.0518 (16)	0.0409 (15)	−0.0078 (15)	−0.0031 (14)	0.0011 (14)
C13	0.085 (3)	0.069 (2)	0.056 (2)	−0.006 (2)	−0.010 (2)	−0.0167 (18)
C14	0.0571 (18)	0.0438 (15)	0.0327 (14)	0.0051 (14)	−0.0022 (13)	−0.0014 (12)
C15	0.077 (2)	0.0559 (18)	0.0441 (16)	0.0182 (18)	−0.0011 (16)	0.0077 (15)
C16	0.074 (2)	0.075 (2)	0.074 (2)	−0.008 (2)	−0.031 (2)	0.000 (2)
C17	0.0574 (18)	0.0465 (16)	0.0373 (14)	0.0096 (14)	0.0063 (14)	0.0057 (13)
C18	0.054 (2)	0.087 (3)	0.080 (2)	−0.007 (2)	0.0077 (18)	0.008 (2)
C19	0.080 (2)	0.066 (2)	0.0462 (17)	0.018 (2)	0.0168 (17)	0.0049 (17)
C20	0.0414 (15)	0.0434 (15)	0.0353 (14)	0.0022 (13)	0.0044 (12)	−0.0009 (12)
C21	0.0415 (15)	0.0402 (14)	0.0347 (13)	0.0003 (12)	−0.0029 (12)	0.0028 (12)
C22	0.0377 (14)	0.0422 (15)	0.0400 (14)	−0.0043 (12)	−0.0001 (12)	−0.0015 (12)
C23	0.0424 (15)	0.0470 (15)	0.0381 (14)	−0.0050 (14)	0.0016 (12)	−0.0020 (13)
C24	0.092 (3)	0.057 (2)	0.062 (2)	−0.020 (2)	0.002 (2)	0.0159 (17)
C25	0.0452 (16)	0.0478 (16)	0.0361 (14)	0.0033 (13)	−0.0030 (13)	0.0012 (12)
C26	0.0502 (19)	0.089 (3)	0.057 (2)	0.0166 (19)	−0.0059 (16)	0.0103 (19)

Geometric parameters (Å, º) top

O1—C1	1.425 (4)	C7—H7A	0.9800
O1—C8	1.434 (3)	C8—C9	1.505 (4)
O2—C1	1.419 (4)	C8—H8A	0.9800
O2—C3	1.430 (5)	C9—C10	1.523 (4)
O3—C4	1.421 (4)	C9—H9A	0.9800
O3—C5	1.434 (5)	C10—H10A	0.9800
O4—C4	1.422 (4)	C11—H11A	0.9600
O4—C7	1.429 (3)	C11—H11B	0.9600
O5—C9	1.437 (4)	C11—H11C	0.9600
O5—H5A	0.8200	C12—C13	1.508 (5)
O6—C10	1.407 (4)	C12—H12B	0.9800
O6—C11	1.417 (5)	C13—H13A	0.9600
O7—C10	1.410 (4)	C13—H13B	0.9600
O7—C12	1.437 (4)	C13—H13C	0.9600
O8—C14	1.423 (3)	C14—C15	1.519 (4)
O8—C21	1.441 (3)	C14—C17	1.555 (4)
O9—C14	1.409 (4)	C15—H15A	0.9600
O9—C16	1.433 (4)	C15—H15B	0.9600
O10—C17	1.414 (4)	C15—H15C	0.9600
O10—C18	1.432 (4)	C16—H16A	0.9600
O11—C17	1.424 (3)	C16—H16B	0.9600
O11—C20	1.438 (3)	C16—H16C	0.9600
O12—C22	1.414 (3)	C17—C19	1.520 (4)
O12—H12A	0.8200	C18—H18A	0.9600
O13—C23	1.406 (3)	C18—H18B	0.9600
O13—C24	1.427 (4)	C18—H18C	0.9600
O14—C23	1.415 (4)	C19—H19A	0.9600
O14—C25	1.444 (3)	C19—H19B	0.9600
C1—C2	1.513 (5)	C19—H19C	0.9600
C1—C4	1.555 (5)	C20—C21	1.501 (4)
C2—H2A	0.9600	C20—C25	1.519 (4)
C2—H2B	0.9600	C20—H20A	0.9800
C2—H2C	0.9600	C21—C22	1.514 (4)
C3—H3A	0.9600	C21—H21A	0.9800
C3—H3B	0.9600	C22—C23	1.518 (4)
C3—H3C	0.9600	C22—H22A	0.9800
C4—C6	1.507 (4)	C23—H23A	0.9800
C5—H5B	0.9600	C24—H24A	0.9600
C5—H5C	0.9600	C24—H24B	0.9600
C5—H5D	0.9600	C24—H24C	0.9600
C6—H6A	0.9600	C25—C26	1.522 (4)
C6—H6B	0.9600	C25—H25A	0.9800
C6—H6C	0.9600	C26—H26A	0.9600
C7—C8	1.500 (4)	C26—H26B	0.9600
C7—C12	1.519 (4)	C26—H26C	0.9600

C1—O1—C8	111.9 (2)	C7—C12—H12B	109.5
C1—O2—C3	116.8 (3)	C12—C13—H13A	109.5
C4—O3—C5	115.0 (3)	C12—C13—H13B	109.5
C4—O4—C7	112.5 (2)	H13A—C13—H13B	109.5
C9—O5—H5A	109.5	C12—C13—H13C	109.5
C10—O6—C11	114.0 (3)	H13A—C13—H13C	109.5
C10—O7—C12	115.4 (2)	H13B—C13—H13C	109.5
C14—O8—C21	112.0 (2)	O9—C14—O8	110.4 (2)
C14—O9—C16	116.4 (3)	O9—C14—C15	112.5 (2)
C17—O10—C18	116.7 (3)	O8—C14—C15	106.3 (2)
C17—O11—C20	112.7 (2)	O9—C14—C17	104.6 (2)
C22—O12—H12A	109.5	O8—C14—C17	110.4 (2)
C23—O13—C24	113.6 (2)	C15—C14—C17	112.7 (3)
C23—O14—C25	115.5 (2)	C14—C15—H15A	109.5
O2—C1—O1	110.0 (3)	C14—C15—H15B	109.5
O2—C1—C2	113.2 (3)	H15A—C15—H15B	109.5
O1—C1—C2	105.4 (3)	C14—C15—H15C	109.5
O2—C1—C4	103.3 (3)	H15A—C15—H15C	109.5
O1—C1—C4	111.7 (2)	H15B—C15—H15C	109.5
C2—C1—C4	113.4 (3)	O9—C16—H16A	109.5
C1—C2—H2A	109.5	O9—C16—H16B	109.5
C1—C2—H2B	109.5	H16A—C16—H16B	109.5
H2A—C2—H2B	109.5	O9—C16—H16C	109.5
C1—C2—H2C	109.5	H16A—C16—H16C	109.5
H2A—C2—H2C	109.5	H16B—C16—H16C	109.5
H2B—C2—H2C	109.5	O10—C17—O11	110.4 (3)
O2—C3—H3A	109.5	O10—C17—C19	113.2 (3)
O2—C3—H3B	109.5	O11—C17—C19	105.4 (2)
H3A—C3—H3B	109.5	O10—C17—C14	103.8 (2)
O2—C3—H3C	109.5	O11—C17—C14	111.7 (2)
H3A—C3—H3C	109.5	C19—C17—C14	112.6 (3)
H3B—C3—H3C	109.5	O10—C18—H18A	109.5
O3—C4—O4	109.8 (3)	O10—C18—H18B	109.5
O3—C4—C6	112.8 (3)	H18A—C18—H18B	109.5
O4—C4—C6	106.3 (3)	O10—C18—H18C	109.5
O3—C4—C1	104.1 (3)	H18A—C18—H18C	109.5
O4—C4—C1	111.1 (2)	H18B—C18—H18C	109.5
C6—C4—C1	112.9 (3)	C17—C19—H19A	109.5
O3—C5—H5B	109.5	C17—C19—H19B	109.5
O3—C5—H5C	109.5	H19A—C19—H19B	109.5
H5B—C5—H5C	109.5	C17—C19—H19C	109.5
O3—C5—H5D	109.5	H19A—C19—H19C	109.5
H5B—C5—H5D	109.5	H19B—C19—H19C	109.5
H5C—C5—H5D	109.5	O11—C20—C21	109.0 (2)
C4—C6—H6A	109.5	O11—C20—C25	108.0 (2)
C4—C6—H6B	109.5	C21—C20—C25	109.9 (2)
H6A—C6—H6B	109.5	O11—C20—H20A	110.0
C4—C6—H6C	109.5	C21—C20—H20A	110.0
H6A—C6—H6C	109.5	C25—C20—H20A	110.0
H6B—C6—H6C	109.5	O8—C21—C20	109.8 (2)
O4—C7—C8	109.2 (2)	O8—C21—C22	109.8 (2)
O4—C7—C12	108.5 (2)	C20—C21—C22	110.4 (2)
C8—C7—C12	110.4 (2)	O8—C21—H21A	108.9
O4—C7—H7A	109.6	C20—C21—H21A	108.9
C8—C7—H7A	109.6	C22—C21—H21A	108.9
C12—C7—H7A	109.6	O12—C22—C21	112.7 (2)
O1—C8—C9	109.6 (2)	O12—C22—C23	106.3 (2)
O1—C8—C7	109.0 (2)	C21—C22—C23	107.3 (2)
C9—C8—C7	111.5 (2)	O12—C22—H22A	110.2
O1—C8—H8A	108.9	C21—C22—H22A	110.2
C9—C8—H8A	108.9	C23—C22—H22A	110.2
C7—C8—H8A	108.9	O13—C23—O14	111.7 (2)
O5—C9—C8	113.0 (2)	O13—C23—C22	106.8 (2)
O5—C9—C10	106.6 (2)	O14—C23—C22	112.5 (2)
C8—C9—C10	108.1 (2)	O13—C23—H23A	108.6
O5—C9—H9A	109.7	O14—C23—H23A	108.6
C8—C9—H9A	109.7	C22—C23—H23A	108.6
C10—C9—H9A	109.7	O13—C24—H24A	109.5
O7—C10—O6	112.6 (3)	O13—C24—H24B	109.5
O7—C10—C9	112.7 (2)	H24A—C24—H24B	109.5
O6—C10—C9	105.4 (3)	O13—C24—H24C	109.5
O7—C10—H10A	108.6	H24A—C24—H24C	109.5
O6—C10—H10A	108.6	H24B—C24—H24C	109.5
C9—C10—H10A	108.6	O14—C25—C20	108.3 (2)
O6—C11—H11A	109.5	O14—C25—C26	106.1 (2)
O6—C11—H11B	109.5	C20—C25—C26	113.3 (3)
H11A—C11—H11B	109.5	O14—C25—H25A	109.7
O6—C11—H11C	109.5	C20—C25—H25A	109.7
H11A—C11—H11C	109.5	C26—C25—H25A	109.7
H11B—C11—H11C	109.5	C25—C26—H26A	109.5
O7—C12—C13	107.1 (3)	C25—C26—H26B	109.5
O7—C12—C7	108.9 (2)	H26A—C26—H26B	109.5
C13—C12—C7	112.3 (3)	C25—C26—H26C	109.5
O7—C12—H12B	109.5	H26A—C26—H26C	109.5
C13—C12—H12B	109.5	H26B—C26—H26C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O13ⁱ	0.82	2.17	2.907 (3)	150
O12—H12A···O5ⁱⁱ	0.82	2.10	2.846 (3)	152

Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₁₃H₂₄O₇
M_r	292.32
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	295
a, b, c (Å)	12.8743 (14), 13.1182 (12), 18.208 (3)
V (Å³)	3075.0 (7)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.6 × 0.5 × 0.4

Data collection
Diffractometer	Bruker P4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.933, 0.994
No. of measured, independent and observed [I > 2s(I)] reflections	3842, 3032, 2630
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.106, 1.02
No. of reflections	3032
No. of parameters	362
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.17

Computer programs: XSCANS (Siemens, 1995), SHELXTL (Sheldrick, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O13ⁱ	0.8200	2.1700	2.907 (3)	150.00
O12—H12A···O5ⁱⁱ	0.8200	2.1000	2.846 (3)	152.00

Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) x, y−1, z.

Acknowledgements

We gratefully acknowledge financial support in part from the National Science Council, Taiwan (NSC 96-2113-M-033-003) and in part from the Project of the Specific Research Fields of Chung Yuan Christian University, Taiwan (CYCU-95-CR-CH).

References

Bauer, J., Brandenburg, K., Zahringer, U. & Rademann, J. (2006). Chem. Eur. J. 12, 7116–7124. Web of Science CrossRef PubMed CAS Google Scholar
Duynstee, H. I., van Vilet, M. J., van der Marel, G. A. & van Boom, J. H. (1998). Eur. J. Org. Chem. pp. 303–307. CrossRef Google Scholar
Lang, S. & Wullbrandt, D. (1999). Appl. Microbiol. Biotechnol. 51, 22–32. CrossRef PubMed CAS Google Scholar
Leisinger, T. & Margraff, R. (1979). Microbiol. Rev. 43, 422–442. PubMed CAS Web of Science Google Scholar
Montchamp, J.-L., Tian, F., Hart, M. E. & Frost, J. W. (1996). J. Org. Chem. 61, 3897–3899. CrossRef PubMed CAS Web of Science Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1995). XSCANS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 5| May 2008| Page o897

doi:10.1107/S1600536808008222

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Methyl (2′S,3′S)-3,4-O-(2′,3′-di­meth­oxy­butane-2′,3′-di­yl)-α-L-rhamno­pyran­oside: a glycosyl acceptor

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Methyl (2′S,3′S)-3,4-O-(2′,3′-dimethoxybutane-2′,3′-diyl)-α-L-rhamnopyranoside: a glycosyl acceptor