Isopropyl 2,3,4,6-tetra-O-acetyl-β-d-glucopyran­oside

Mönch, B.; Emmerling, F.; Kraus, W.; Becker, R.; Nehls, I.

doi:10.1107/S1600536812051483

organic compounds

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ISSN: 2056-9890

Volume 69| Part 2| February 2013| Page o157

doi:10.1107/S1600536812051483

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Isopropyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

Bettina Mönch,^a Franziska Emmerling,^a ^* Werner Kraus,^a Roland Becker ^a and Irene Nehls ^a

^aBAM Federal Institute for Materials Research and Testing, Department of Analytical Chemistry, Reference Materials, Richard-Willstätter-Strasse 11, D-12489 Berlin, Germany
^*Correspondence e-mail: franziska.emmerling@bam.de

(Received 26 November 2012; accepted 20 December 2012; online 4 January 2013)

The title compound, C₁₇H₂₆O₁₀, was formed by a Koenigs–Knorr reaction of 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide and propan-2-ol. The central ring adopts a chair conformation. The crystal does not contain any significant intermolecular interactions.

Related literature

Metabolites of alcohol are important markers for previous alcohol consumption, see: Joya et al. (2012 ); Helander et al. (2012 ). For investigation of the short-chain alkyl alcohol content in alcoholic beverages, see: Lachenmeier & Musshoff (2004 ). For the relevance of short-chain alkyl alcohol glucuronides as alcohol markers, see; Sticht & Käferstein (1999 ). For related synthesis, see: Baer & Abbas (1979 ).

Experimental

Crystal data

C₁₇H₂₆O₁₀
M_r = 390.38
Monoclinic, P 2₁
a = 9.4225 (12) Å
b = 9.9313 (12) Å
c = 11.3641 (15) Å
β = 98.482 (9)°
V = 1051.8 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 K
0.28 × 0.12 × 0.11 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.221, T_max = 0.364
11225 measured reflections
2274 independent reflections
1411 reflections with I > 2σ(I)
R_int = 0.107

Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.151
S = 1.07
2274 reflections
244 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Data collection: APEX2 (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and ORTEPIII (Burnett & Johnson, 1996 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812051483/bt6870sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812051483/bt6870Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812051483/bt6870Isup3.mol

checkCIF report

Comment top

In recent years the determination of alcohol metabolites gained importance for screening previous alcohol consumption (Joya et al., Helander et al., 2012). Beside ethanol several short-chain alkyl alcohols, e.g. i-propanol, are found in alcoholic beverages as a result of the fermentation process (Lachenmeier & Musshoff, 2004). The glucuronides of these so-called fusel alcohols are interesting markers for the consumption of alcohol (Sticht & Käferstein, 1999). Hence, the analysis of these glucuronic metabolites, including their synthesis and full characterization is mandatory.

The title compound was formed by a Koenigs-Knorr-reaction of 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide and propan-2-ol (related synthesis Baer & Abbas, 1979) as an intermediate product towards synthesis of n-propyl-glucuronide.

The central ring has a chair conformation (Fig 1). The absolute configuration could not be defined confidently based on the single-crystal diffraction data. The isomeric purity of the title compound was confirmed by ¹H-NMR.

Related literature top

Metabolites of alcohol are important markers for previous alcohol consumption, see: Joya et al. (2012); Helander et al. (2012). For investigation of the short-chain alkyl alcohol content in alcoholic beverages, see: Lachenmeier & Musshoff (2004). For the relevance of short-chain alkyl alcohol glucuronides as alcohol markers, see; Sticht & Käferstein (1999). For related synthesis, see: Baer & Abbas (1979).

Experimental top

i-Propyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside was synthesized by a Koenigs-Knorr-reaction of 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide and propan-2-ol. In order to obtain crystals suitable for single-crystal analysis, about 10 mg of the compound were dissolved in 2 ml propan-2-ol. Colourless crystals of the title compound were formed after 4 days of slow solvent evaporation at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and ORTEPIII (Burnett & Johnson,1996); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. ORTEP representation of the title compound with atomic labeling shown with 30% probability displacement ellipsoids.
	Fig. 2. View of the unit cell of the title compound along the b axis.

Isopropyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside top

Crystal data top

C₁₇H₂₆O₁₀	F(000) = 416
M_r = 390.38	D_x = 1.233 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 9.4225 (12) Å	Cell parameters from 1344 reflections
b = 9.9313 (12) Å	θ = 2.6–19.8°
c = 11.3641 (15) Å	µ = 0.10 mm⁻¹
β = 98.482 (9)°	T = 296 K
V = 1051.8 (2) Å³	Block, colourless
Z = 2	0.28 × 0.12 × 0.11 mm

Data collection top

Bruker APEXII CCD diffractometer	2274 independent reflections
Radiation source: fine-focus sealed tube	1411 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.107
ϕ and ω scans	θ_max = 26.3°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −11→11
T_min = 0.221, T_max = 0.364	k = −12→11
11225 measured reflections	l = −14→14

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.151	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0659P)²] where P = (F_o² + 2F_c²)/3
2274 reflections	(Δ/σ)_max < 0.001
244 parameters	Δρ_max = 0.16 e Å⁻³
1 restraint	Δρ_min = −0.13 e Å⁻³

Crystal data top

C₁₇H₂₆O₁₀	V = 1051.8 (2) Å³
M_r = 390.38	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 9.4225 (12) Å	µ = 0.10 mm⁻¹
b = 9.9313 (12) Å	T = 296 K
c = 11.3641 (15) Å	0.28 × 0.12 × 0.11 mm
β = 98.482 (9)°

Data collection top

Bruker APEXII CCD diffractometer	2274 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	1411 reflections with I > 2σ(I)
T_min = 0.221, T_max = 0.364	R_int = 0.107
11225 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	1 restraint
wR(F²) = 0.151	H-atom parameters constrained
S = 1.07	Δρ_max = 0.16 e Å⁻³
2274 reflections	Δρ_min = −0.13 e Å⁻³
244 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	0.5370 (3)	0.1530 (3)	0.2024 (3)	0.0679 (9)
O2	0.4905 (5)	0.3603 (4)	0.1307 (4)	0.1009 (14)
O3	0.7120 (3)	0.2202 (3)	0.4275 (3)	0.0599 (8)
O4	0.8668 (4)	0.0492 (4)	0.4350 (5)	0.1119 (16)
O5	0.6214 (3)	0.0547 (3)	0.6176 (3)	0.0608 (8)
O6	0.6978 (6)	0.2424 (5)	0.7143 (4)	0.1298 (19)
O7	0.2892 (3)	0.1260 (3)	0.4196 (3)	0.0651 (8)
O8	0.2399 (3)	0.1684 (3)	0.2197 (3)	0.0696 (9)
O9	0.3094 (4)	0.1908 (3)	0.6722 (3)	0.0752 (10)
O10	0.1637 (7)	0.1219 (6)	0.7944 (5)	0.149 (2)
C1	0.5300 (6)	0.2489 (6)	0.1162 (5)	0.0727 (14)
C2	0.5743 (7)	0.1902 (8)	0.0060 (5)	0.108 (2)
H2A	0.5697	0.2584	−0.0542	0.161*
H2B	0.5109	0.1176	−0.0220	0.161*
H2C	0.6707	0.1568	0.0235	0.161*
C3	0.4811 (4)	0.1820 (4)	0.3120 (4)	0.0542 (11)
H3A	0.4669	0.2792	0.3197	0.065*
C4	0.5889 (4)	0.1315 (4)	0.4138 (4)	0.0514 (10)
H4A	0.6193	0.0404	0.3959	0.062*
C5	0.8464 (5)	0.1663 (6)	0.4401 (5)	0.0709 (14)
C6	0.9581 (6)	0.2722 (6)	0.4646 (7)	0.104 (2)
H6A	1.0514	0.2314	0.4728	0.156*
H6B	0.9468	0.3183	0.5368	0.156*
H6C	0.9483	0.3353	0.3999	0.156*
C7	0.5271 (4)	0.1297 (4)	0.5294 (4)	0.0526 (10)
H7A	0.5172	0.2221	0.5572	0.063*
C8	0.7049 (6)	0.1238 (7)	0.7044 (5)	0.0780 (15)
C9	0.8026 (6)	0.0292 (7)	0.7811 (5)	0.095 (2)
H9A	0.8613	0.0794	0.8420	0.143*
H9B	0.8626	−0.0172	0.7331	0.143*
H9C	0.7462	−0.0350	0.8171	0.143*
C10	0.3795 (5)	0.0587 (5)	0.5137 (4)	0.0574 (11)
H10A	0.3926	−0.0345	0.4892	0.069*
C11	0.3396 (5)	0.1088 (5)	0.3077 (4)	0.0580 (11)
H11A	0.3509	0.0130	0.2907	0.070*
C12	0.1157 (6)	0.0848 (6)	0.1770 (5)	0.0838 (17)
H12A	0.0844	0.0373	0.2443	0.101*
C13	0.0007 (7)	0.1795 (8)	0.1244 (7)	0.133 (3)
H13A	−0.0210	0.2409	0.1846	0.199*
H13B	−0.0839	0.1295	0.0938	0.199*
H13C	0.0331	0.2293	0.0610	0.199*
C14	0.1516 (9)	−0.0151 (8)	0.0883 (7)	0.132 (3)
H14A	0.2236	−0.0758	0.1259	0.198*
H14B	0.1874	0.0312	0.0245	0.198*
H14C	0.0671	−0.0649	0.0572	0.198*
C15	0.3091 (6)	0.0569 (5)	0.6241 (5)	0.0708 (14)
H15A	0.2113	0.0246	0.6051	0.085*
H15B	0.3609	−0.0034	0.6825	0.085*
C16	0.2309 (6)	0.2104 (7)	0.7598 (5)	0.0852 (17)
C17	0.2438 (9)	0.3493 (7)	0.8081 (6)	0.119 (3)
H17A	0.1849	0.3584	0.8698	0.178*
H17B	0.2127	0.4124	0.7456	0.178*
H17C	0.3420	0.3671	0.8403	0.178*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.071 (2)	0.073 (2)	0.0601 (19)	0.0155 (19)	0.0089 (16)	0.0013 (19)
O2	0.137 (4)	0.075 (3)	0.093 (3)	0.009 (3)	0.025 (3)	0.022 (2)
O3	0.0504 (17)	0.0541 (18)	0.075 (2)	0.0007 (15)	0.0081 (15)	0.0020 (16)
O4	0.069 (2)	0.069 (3)	0.197 (5)	0.014 (2)	0.016 (3)	−0.005 (3)
O5	0.0677 (18)	0.0512 (17)	0.060 (2)	−0.0004 (16)	−0.0015 (17)	0.0015 (17)
O6	0.190 (5)	0.077 (3)	0.104 (4)	−0.003 (3)	−0.039 (3)	−0.021 (3)
O7	0.0547 (17)	0.0625 (19)	0.077 (2)	−0.0016 (16)	0.0072 (16)	0.0041 (19)
O8	0.0603 (18)	0.061 (2)	0.081 (2)	−0.0050 (16)	−0.0111 (17)	0.0118 (18)
O9	0.084 (2)	0.064 (2)	0.084 (2)	0.0017 (19)	0.035 (2)	0.006 (2)
O10	0.176 (5)	0.149 (4)	0.144 (5)	−0.045 (4)	0.099 (4)	−0.011 (4)
C1	0.071 (3)	0.080 (4)	0.067 (4)	0.001 (3)	0.009 (3)	0.010 (3)
C2	0.117 (5)	0.133 (6)	0.077 (4)	0.017 (5)	0.027 (4)	0.005 (4)
C3	0.059 (2)	0.050 (2)	0.054 (3)	0.006 (2)	0.009 (2)	0.000 (2)
C4	0.053 (2)	0.044 (2)	0.057 (3)	−0.001 (2)	0.008 (2)	0.001 (2)
C5	0.056 (3)	0.074 (4)	0.083 (4)	0.013 (3)	0.010 (3)	0.000 (3)
C6	0.055 (3)	0.084 (4)	0.170 (7)	−0.003 (3)	0.003 (4)	−0.007 (4)
C7	0.056 (2)	0.041 (2)	0.059 (3)	0.006 (2)	0.000 (2)	0.002 (2)
C8	0.086 (4)	0.076 (4)	0.069 (4)	−0.009 (3)	0.000 (3)	−0.004 (3)
C9	0.080 (4)	0.125 (5)	0.074 (4)	−0.006 (4)	−0.013 (3)	0.013 (4)
C10	0.059 (3)	0.042 (2)	0.070 (3)	0.000 (2)	0.007 (2)	0.009 (2)
C11	0.063 (3)	0.046 (2)	0.063 (3)	−0.001 (2)	0.001 (2)	0.003 (2)
C12	0.076 (3)	0.083 (4)	0.082 (4)	−0.020 (3)	−0.022 (3)	0.017 (3)
C13	0.078 (4)	0.155 (7)	0.148 (7)	−0.014 (5)	−0.043 (4)	0.015 (6)
C14	0.167 (8)	0.108 (5)	0.104 (6)	−0.009 (5)	−0.034 (5)	−0.016 (5)
C15	0.070 (3)	0.064 (3)	0.080 (4)	−0.005 (3)	0.018 (3)	0.010 (3)
C16	0.081 (4)	0.099 (5)	0.078 (4)	0.004 (4)	0.022 (3)	0.013 (4)
C17	0.163 (7)	0.098 (5)	0.104 (5)	0.029 (5)	0.049 (5)	−0.005 (4)

Geometric parameters (Å, º) top

O1—C1	1.361 (6)	C6—H6B	0.9600
O1—C3	1.451 (5)	C6—H6C	0.9600
O2—C1	1.187 (6)	C7—C10	1.546 (6)
O3—C5	1.363 (6)	C7—H7A	0.9800
O3—C4	1.446 (5)	C8—C9	1.500 (8)
O4—C5	1.181 (6)	C9—H9A	0.9600
O5—C8	1.354 (6)	C9—H9B	0.9600
O5—C7	1.445 (5)	C9—H9C	0.9600
O6—C8	1.187 (7)	C10—C15	1.503 (6)
O7—C10	1.431 (5)	C10—H10A	0.9800
O7—C11	1.432 (5)	C11—H11A	0.9800
O8—C11	1.398 (5)	C12—C14	1.489 (9)
O8—C12	1.459 (6)	C12—C13	1.491 (8)
O9—C16	1.339 (6)	C12—H12A	0.9800
O9—C15	1.438 (6)	C13—H13A	0.9600
O10—C16	1.184 (7)	C13—H13B	0.9600
C1—C2	1.495 (8)	C13—H13C	0.9600
C2—H2A	0.9600	C14—H14A	0.9600
C2—H2B	0.9600	C14—H14B	0.9600
C2—H2C	0.9600	C14—H14C	0.9600
C3—C4	1.508 (6)	C15—H15A	0.9700
C3—C11	1.514 (6)	C15—H15B	0.9700
C3—H3A	0.9800	C16—C17	1.484 (9)
C4—C7	1.513 (6)	C17—H17A	0.9600
C4—H4A	0.9800	C17—H17B	0.9600
C5—C6	1.485 (8)	C17—H17C	0.9600
C6—H6A	0.9600

C1—O1—C3	119.6 (4)	C8—C9—H9C	109.5
C5—O3—C4	119.4 (4)	H9A—C9—H9C	109.5
C8—O5—C7	118.5 (4)	H9B—C9—H9C	109.5
C10—O7—C11	111.7 (3)	O7—C10—C15	110.1 (4)
C11—O8—C12	114.8 (3)	O7—C10—C7	107.4 (3)
C16—O9—C15	116.5 (4)	C15—C10—C7	114.2 (4)
O2—C1—O1	122.4 (5)	O7—C10—H10A	108.4
O2—C1—C2	127.7 (6)	C15—C10—H10A	108.4
O1—C1—C2	109.9 (5)	C7—C10—H10A	108.4
C1—C2—H2A	109.5	O8—C11—O7	108.0 (4)
C1—C2—H2B	109.5	O8—C11—C3	108.4 (3)
H2A—C2—H2B	109.5	O7—C11—C3	108.6 (3)
C1—C2—H2C	109.5	O8—C11—H11A	110.6
H2A—C2—H2C	109.5	O7—C11—H11A	110.6
H2B—C2—H2C	109.5	C3—C11—H11A	110.6
O1—C3—C4	107.7 (3)	O8—C12—C14	110.7 (5)
O1—C3—C11	107.8 (3)	O8—C12—C13	105.9 (5)
C4—C3—C11	110.9 (3)	C14—C12—C13	111.9 (6)
O1—C3—H3A	110.1	O8—C12—H12A	109.4
C4—C3—H3A	110.1	C14—C12—H12A	109.4
C11—C3—H3A	110.1	C13—C12—H12A	109.4
O3—C4—C3	108.6 (3)	C12—C13—H13A	109.5
O3—C4—C7	108.6 (3)	C12—C13—H13B	109.5
C3—C4—C7	111.6 (3)	H13A—C13—H13B	109.5
O3—C4—H4A	109.3	C12—C13—H13C	109.5
C3—C4—H4A	109.3	H13A—C13—H13C	109.5
C7—C4—H4A	109.3	H13B—C13—H13C	109.5
O4—C5—O3	122.4 (5)	C12—C14—H14A	109.5
O4—C5—C6	126.2 (5)	C12—C14—H14B	109.5
O3—C5—C6	111.3 (5)	H14A—C14—H14B	109.5
C5—C6—H6A	109.5	C12—C14—H14C	109.5
C5—C6—H6B	109.5	H14A—C14—H14C	109.5
H6A—C6—H6B	109.5	H14B—C14—H14C	109.5
C5—C6—H6C	109.5	O9—C15—C10	109.2 (4)
H6A—C6—H6C	109.5	O9—C15—H15A	109.8
H6B—C6—H6C	109.5	C10—C15—H15A	109.8
O5—C7—C4	109.4 (3)	O9—C15—H15B	109.8
O5—C7—C10	107.2 (3)	C10—C15—H15B	109.8
C4—C7—C10	111.1 (3)	H15A—C15—H15B	108.3
O5—C7—H7A	109.7	O10—C16—O9	121.4 (6)
C4—C7—H7A	109.7	O10—C16—C17	125.9 (6)
C10—C7—H7A	109.7	O9—C16—C17	112.7 (6)
O6—C8—O5	122.5 (6)	C16—C17—H17A	109.5
O6—C8—C9	127.2 (6)	C16—C17—H17B	109.5
O5—C8—C9	110.3 (5)	H17A—C17—H17B	109.5
C8—C9—H9A	109.5	C16—C17—H17C	109.5
C8—C9—H9B	109.5	H17A—C17—H17C	109.5
H9A—C9—H9B	109.5	H17B—C17—H17C	109.5

Experimental details

Crystal data
Chemical formula	C₁₇H₂₆O₁₀
M_r	390.38
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	296
a, b, c (Å)	9.4225 (12), 9.9313 (12), 11.3641 (15)
β (°)	98.482 (9)
V (Å³)	1051.8 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.28 × 0.12 × 0.11

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.221, 0.364
No. of measured, independent and observed [I > 2σ(I)] reflections	11225, 2274, 1411
R_int	0.107
(sin θ/λ)_max (Å⁻¹)	0.624

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.151, 1.07
No. of reflections	2274
No. of parameters	244
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.13

Computer programs: APEX2 (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and ORTEPIII (Burnett & Johnson,1996), SHELXTL (Sheldrick, 2008).

References

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