(3S,4S,5S)-4-Hydr­oxy-3-methyl-5-[(2S,3R)-3-methyl­pent-4-en-2-yl]-4,5-dihydro­furan-2(3H)-one

Gille, A.; Schürmann, M.; Preut, H.; Hiersemann, M.

doi:10.1107/S1600536808026998

organic compounds

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Volume 64| Part 9| September 2008| Page o1835

doi:10.1107/S1600536808026998

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(3S,4S,5S)-4-Hydroxy-3-methyl-5-[(2S,3R)-3-methylpent-4-en-2-yl]-4,5-dihydrofuran-2(3H)-one

Annika Gille,^a Markus Schürmann,^a Hans Preut ^a ^* and Martin Hiersemann ^a

^aFakultät Chemie, Technische Universität Dortmund, Otto-Hahn-Str. 6, 44221 Dortmund, Germany
^*Correspondence e-mail: hans.preut@udo.edu

(Received 11 August 2008; accepted 21 August 2008; online 30 August 2008)

The title compound, C₁₁H₁₈O₃, was synthesized to prove the relative configuration of the corresponding acyclic C1—C8 stereopentade. Molecules are linked via O—H⋯O hydrogen bonds, forming a chain along the b axis.

Related literature

For related literature, see: Abraham et al. (2004a ,b ); Corey & Snider (1972 ); Evans et al. (1981 , 1999 ); Körner & Hiersemann (2006 , 2007 ); Pollex & Hiersemann (2005 ).

Experimental

Crystal data

C₁₁H₁₈O₃
M_r = 198.25
Orthorhombic, P 2₁ 2₁ 2₁
a = 5.4414 (14) Å
b = 10.132 (2) Å
c = 20.975 (8) Å
V = 1156.4 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 291 (1) K
0.36 × 0.06 × 0.02 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: none
7554 measured reflections
1223 independent reflections
346 reflections with I > 2σ(I)
R_int = 0.048

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.087
S = 0.97
1223 reflections
131 parameters
H-atom parameters constrained
Δρ_max = 0.09 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O2ⁱ	0.82	2.02	2.798 (6)	158
Symmetry code: (i) $[-x+1, y-{\script{1\over 2}}, -z-{\script{1\over 2}}]$ .

Data collection: COLLECT (Nonius, 1998 ); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997 ); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808026998/bt2768sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808026998/bt2768Isup2.hkl

checkCIF report

Comment top

The title compound, (I), was synthesized using a catalytic asymmetric Claisen rearrangement (Abraham et al., 2004a; Abraham et al., 2004b; Pollex & Hiersemann, 2005; Körner & Hiersemann, 2006; Körner & Hiersemann, 2007), a diastereoselective reduction with K-Selectride (Körner & Hiersemann, 2006; Körner & Hiersemann, 2007), and an Evans aldol addition (Evans et al., 1981). In order to verify the relative configuration of the obtained aldol adduct, 4-(tert-butyldimethylsilyloxy)-3-hydroxy-2,5,6-trimethyloct-7-enoyl)-4-isopropyloxazolidin-2-one, (II), a γ-lactone, (I), was prepared by removal of the silyl protecting group (Corey & Snider, 1972) and subsequent in situ lactonization. Fig. 1 depicts the structure of the isolated major diastereomer (I). The configuration of the chiral C atoms in (I) can be attributed to the stereochemical course of the Evans aldol addition (C3 S and C4 S), the diastereoselective reduction with K-Selectride (C5 S), and the catalytic asymmetric Claisen rearrangement (C(2) S and C(3) R) using the chiral Lewis acid [Cu{(S,S)-tert-Butyl-box}](H₂O)₂(SbF₆)₂ (Evans et al., 1999).

Related literature top

For related literature, see: Abraham et al. (2004a,b); Corey & Snider (1972); Evans et al. (1981, 1999); Körner & Hiersemann (2006, 2007); Pollex & Hiersemann (2005).

Experimental top

The title compound, (I), was synthesized from the corresponding syn-aldol adduct, (II), using tetrabutylammonium fluoride (Corey & Snider, 1972) for the removal of the silyl protecting group. The subsequent lactonization proceeded in situ.

To a solution of diastereomerically pure (II) (50 mg, 0.113 mmol, 1.0 eq) in dry tetrahydrofuran (1 ml) was added TBAF (1 M in tetrahydrofuran, 0.34 ml, 3.0 eq) at 273 K. The mixture was stirred at 273 K for 25 min. The reaction was then quenched by the addition of sat. aqueous NaHCO₃ solution. The phases were separated, and the aqueous phase was extracted with CH₂Cl₂. The combined organic layers were dried over MgSO₄ and concentrated under reduced pressure. Flash chromatography (isohexane/ethyl acetate 20/1 to 10/1) afforded (I) as a single diastereomer and additionally a mixture of (I) and the minor diastereomer with an overall yield of 96% (21.4 mg, 0.108 mmol) as colourless crystals. Single crystals of (I) were obtained by vapor diffusion recrystallization technique from isohexane and ethyl acetate to yield colourless needles: mp 374 K; R_f 0.28 (cyclohexane/ethyl acetate 2/1); ¹H NMR (CDCl₃, 400 MHz, δ): 0.83 (d, J = 7.0 Hz, 3H), 0.98 (d, J = 6.8 Hz, 3H), 1.30 (d, J = 7.8 Hz, 3H), 2.21 (dqd, J = 10.7, 7.0, 3.3 Hz, 1H), 2.64 (q, J = 7.8 Hz, 1H) overlapped by 2.61 - 2.76 (m, 1H), 4.14 (d, J = 3.4 Hz, 1H), 4.23 (dd, J = 10.7, 3.4 Hz, 1H), 5.04 (dd, ³J(Z) = 11.0 Hz, ²J = 1.5 Hz, 1H), 5.05 (dd, ³J(E) = 17.0 Hz, ²J = 1.5 Hz, 1H), 5.84 (ddd, ³J(E) = 17.0 Hz, ³J(Z) = 11.0 Hz, ³J = 6.3 Hz, 1H); ¹³C NMR (CDCl₃, 100 MHz, δ): 9.8 (CH₃), 12.5 (CH₃), 13.7 (CH₃), 35.6 (CH), 37.2 (CH), 46.5 (CH), 75.0 (CH), 83.9 (CH), 114.4 (CH₂), 142.7 (CH), 179.1 (C); IR (cm^-1): 3520(br,s) (ν O—H, OH in H-bridges), 3085(w) (ν C—H, olefin), 2975(m) 2940(m) 2885(s) 2855(w) (ν_as,s C—H, CH₂, CH₃, CH), 1755(s) (ν C=O, lactone), 1640(w) (ν C=C), 1455(m) (δ_as C—H, CH₃, CH₂), 1385(m) (δ_s C—H, CH₃); Anal. Calcd. for C₁₁H₁₈O₃: C, 66.6; H, 9.2; Found: C, 66.5; H, 9.3; [α]_D²⁰ -14.5 (c 0.775, CHCl₃).

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2003).

Figures top

Fig. 1. : The molecular structure of the title compound, showing the labelling of all non-H atoms. Displacement ellipsoids are shown at the 30% probability level.

(3S,4S,5S)-4-Hydroxy-3-methyl-5-[(2S,3R)-3- methylpent-4-en-2-yl]-4,5-dihydrofuran-2(3H)-one top

Crystal data top

C₁₁H₁₈O₃	F(000) = 432
M_r = 198.25	D_x = 1.139 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 7554 reflections
a = 5.4414 (14) Å	θ = 2.8–25.0°
b = 10.132 (2) Å	µ = 0.08 mm⁻¹
c = 20.975 (8) Å	T = 291 K
V = 1156.4 (6) Å³	Needle, colourless
Z = 4	0.36 × 0.06 × 0.02 mm

Data collection top

Nonius KappaCCD diffractometer	346 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.048
Graphite monochromator	θ_max = 25.0°, θ_min = 2.8°
Detector resolution: 19 vertical, 18 horizontal pixels mm^-1	h = −6→6
111 frames via ω–rotation (Δω=2%) and two times 180 s per frame (three sets at different κ–angles) scans	k = −12→12
7554 measured reflections	l = −24→24
1223 independent reflections

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.087	H-atom parameters constrained
S = 0.97	[1.0 exp(5.65(sinθ/λ)²)]/[σ²(F_o²)]
1223 reflections	(Δ/σ)_max = 0.007
131 parameters	Δρ_max = 0.09 e Å⁻³
0 restraints	Δρ_min = −0.13 e Å⁻³

Crystal data top

C₁₁H₁₈O₃	V = 1156.4 (6) Å³
M_r = 198.25	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 5.4414 (14) Å	µ = 0.08 mm⁻¹
b = 10.132 (2) Å	T = 291 K
c = 20.975 (8) Å	0.36 × 0.06 × 0.02 mm

Data collection top

Nonius KappaCCD diffractometer	346 reflections with I > 2σ(I)
7554 measured reflections	R_int = 0.048
1223 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.087	H-atom parameters constrained
S = 0.97	Δρ_max = 0.09 e Å⁻³
1223 reflections	Δρ_min = −0.13 e Å⁻³
131 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	0.1778 (7)	0.0092 (4)	−0.3153 (2)	0.0647 (11)
O2	0.4408 (8)	0.0462 (4)	−0.2370 (2)	0.0971 (19)
O3	0.3095 (10)	−0.2710 (5)	−0.3391 (2)	0.0890 (15)
H3	0.4090	−0.3080	−0.3158	0.133*
C1	0.2948 (12)	−0.0261 (7)	−0.2615 (3)	0.075 (2)
C2	0.2076 (11)	−0.1595 (6)	−0.2396 (3)	0.0641 (19)
H2A	0.3449	−0.2114	−0.2227	0.077*
C3	0.1142 (11)	−0.2191 (6)	−0.3017 (3)	0.0635 (19)
H3B	−0.0147	−0.2849	−0.2942	0.076*
C4	0.0156 (11)	−0.0982 (5)	−0.3372 (3)	0.0596 (18)
H4A	−0.1522	−0.0803	−0.3227	0.072*
C5	0.0176 (10)	−0.1020 (6)	−0.4090 (3)	0.0578 (17)
H5A	0.1854	−0.1235	−0.4225	0.069*
C6	−0.0502 (11)	0.0338 (6)	−0.4390 (3)	0.069 (2)
H6A	0.0627	0.0986	−0.4205	0.082*
C7	0.0064 (15)	0.0286 (7)	−0.5094 (4)	0.107 (3)
H7A	0.1591	−0.0070	−0.5193	0.129*
C8	−0.1131 (18)	0.0629 (9)	−0.5549 (4)	0.170 (4)
H8A	−0.2681	0.0996	−0.5491	0.205*
H8B	−0.0501	0.0527	−0.5958	0.205*
C9	0.0066 (12)	−0.1412 (5)	−0.1883 (3)	0.093 (2)
H9A	−0.0491	−0.2261	−0.1740	0.140*
H9B	−0.1291	−0.0932	−0.2062	0.140*
H9C	0.0731	−0.0929	−0.1529	0.140*
C10	−0.1534 (11)	−0.2165 (5)	−0.4322 (3)	0.085 (2)
H10A	−0.0821	−0.2998	−0.4207	0.128*
H10B	−0.1712	−0.2119	−0.4777	0.128*
H10C	−0.3118	−0.2079	−0.4125	0.128*
C11	−0.3096 (12)	0.0798 (6)	−0.4222 (3)	0.102 (3)
H11A	−0.3376	0.1657	−0.4401	0.152*
H11B	−0.3269	0.0840	−0.3767	0.152*
H11C	−0.4273	0.0187	−0.4393	0.152*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.064 (3)	0.056 (3)	0.074 (3)	−0.002 (3)	−0.011 (3)	−0.006 (2)
O2	0.091 (4)	0.110 (4)	0.091 (4)	−0.027 (3)	−0.026 (3)	−0.012 (3)
O3	0.105 (4)	0.080 (3)	0.083 (3)	0.034 (3)	0.005 (3)	0.002 (3)
C1	0.062 (6)	0.083 (6)	0.081 (6)	0.010 (5)	−0.004 (5)	−0.010 (5)
C2	0.073 (5)	0.065 (5)	0.054 (5)	0.008 (4)	−0.013 (4)	0.009 (3)
C3	0.072 (5)	0.048 (4)	0.071 (5)	0.000 (4)	0.009 (4)	0.005 (4)
C4	0.053 (5)	0.056 (4)	0.070 (5)	0.000 (4)	0.002 (4)	−0.006 (4)
C5	0.039 (4)	0.068 (4)	0.066 (5)	0.001 (4)	−0.002 (4)	−0.008 (4)
C6	0.072 (6)	0.073 (4)	0.061 (5)	0.005 (4)	−0.013 (4)	0.009 (4)
C7	0.133 (7)	0.106 (6)	0.082 (7)	0.050 (6)	−0.028 (6)	0.007 (5)
C8	0.233 (13)	0.159 (9)	0.119 (10)	−0.006 (8)	−0.019 (9)	0.019 (7)
C9	0.119 (7)	0.089 (5)	0.071 (6)	0.002 (5)	0.021 (6)	0.004 (4)
C10	0.094 (6)	0.078 (5)	0.084 (5)	−0.016 (4)	−0.015 (5)	−0.013 (4)
C11	0.085 (6)	0.111 (6)	0.109 (6)	0.048 (5)	0.007 (5)	0.021 (4)

Geometric parameters (Å, º) top

O1—C1	1.344 (6)	C6—C7	1.508 (8)
O1—C4	1.475 (6)	C6—C11	1.527 (6)
O2—C1	1.196 (6)	C6—H6A	0.9800
O3—C3	1.422 (6)	C7—C8	1.207 (8)
O3—H3	0.8200	C7—H7A	0.9300
C1—C2	1.504 (7)	C8—H8A	0.9300
C2—C3	1.523 (7)	C8—H8B	0.9300
C2—C9	1.546 (7)	C9—H9A	0.9600
C2—H2A	0.9800	C9—H9B	0.9600
C3—C4	1.531 (6)	C9—H9C	0.9600
C3—H3B	0.9800	C10—H10A	0.9600
C4—C5	1.506 (6)	C10—H10B	0.9600
C4—H4A	0.9800	C10—H10C	0.9600
C5—C6	1.557 (6)	C11—H11A	0.9600
C5—C10	1.564 (7)	C11—H11B	0.9600
C5—H5A	0.9800	C11—H11C	0.9600

C1—O1—C4	110.5 (5)	C7—C6—C5	108.4 (5)
C3—O3—H3	109.5	C11—C6—C5	113.3 (5)
O2—C1—O1	120.8 (7)	C7—C6—H6A	106.5
O2—C1—C2	129.0 (7)	C11—C6—H6A	106.5
O1—C1—C2	110.2 (6)	C5—C6—H6A	106.5
C1—C2—C3	101.6 (5)	C8—C7—C6	130.9 (9)
C1—C2—C9	109.1 (5)	C8—C7—H7A	114.6
C3—C2—C9	114.0 (6)	C6—C7—H7A	114.6
C1—C2—H2A	110.6	C7—C8—H8A	120.0
C3—C2—H2A	110.6	C7—C8—H8B	120.0
C9—C2—H2A	110.6	H8A—C8—H8B	120.0
O3—C3—C2	111.7 (5)	C2—C9—H9A	109.5
O3—C3—C4	106.8 (5)	C2—C9—H9B	109.5
C2—C3—C4	102.5 (5)	H9A—C9—H9B	109.5
O3—C3—H3B	111.8	C2—C9—H9C	109.5
C2—C3—H3B	111.8	H9A—C9—H9C	109.5
C4—C3—H3B	111.8	H9B—C9—H9C	109.5
O1—C4—C5	109.1 (5)	C5—C10—H10A	109.5
O1—C4—C3	103.2 (4)	C5—C10—H10B	109.5
C5—C4—C3	117.6 (5)	H10A—C10—H10B	109.5
O1—C4—H4A	108.8	C5—C10—H10C	109.5
C5—C4—H4A	108.8	H10A—C10—H10C	109.5
C3—C4—H4A	108.8	H10B—C10—H10C	109.5
C4—C5—C6	112.3 (5)	C6—C11—H11A	109.5
C4—C5—C10	109.0 (5)	C6—C11—H11B	109.5
C6—C5—C10	112.8 (5)	H11A—C11—H11B	109.5
C4—C5—H5A	107.5	C6—C11—H11C	109.5
C6—C5—H5A	107.5	H11A—C11—H11C	109.5
C10—C5—H5A	107.5	H11B—C11—H11C	109.5
C7—C6—C11	115.1 (5)

C4—O1—C1—O2	177.8 (6)	C2—C3—C4—O1	31.7 (6)
C4—O1—C1—C2	−3.8 (7)	O3—C3—C4—C5	34.3 (8)
O2—C1—C2—C3	−157.8 (7)	C2—C3—C4—C5	151.8 (5)
O1—C1—C2—C3	24.0 (7)	O1—C4—C5—C6	−54.5 (6)
O2—C1—C2—C9	81.5 (9)	C3—C4—C5—C6	−171.5 (5)
O1—C1—C2—C9	−96.7 (6)	O1—C4—C5—C10	179.7 (5)
C1—C2—C3—O3	80.8 (6)	C3—C4—C5—C10	62.7 (7)
C9—C2—C3—O3	−162.0 (5)	C4—C5—C6—C7	168.6 (6)
C1—C2—C3—C4	−33.2 (6)	C10—C5—C6—C7	−67.7 (7)
C9—C2—C3—C4	84.0 (6)	C4—C5—C6—C11	−62.3 (7)
C1—O1—C4—C5	−143.8 (5)	C10—C5—C6—C11	61.4 (7)
C1—O1—C4—C3	−18.0 (6)	C11—C6—C7—C8	5.6 (14)
O3—C3—C4—O1	−85.8 (5)	C5—C6—C7—C8	133.7 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2ⁱ	0.82	2.02	2.798 (6)	158

Symmetry code: (i) −x+1, y−1/2, −z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₁H₁₈O₃
M_r	198.25
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	291
a, b, c (Å)	5.4414 (14), 10.132 (2), 20.975 (8)
V (Å³)	1156.4 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.36 × 0.06 × 0.02

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	7554, 1223, 346
R_int	0.048
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.087, 0.97
No. of reflections	1223
No. of parameters	131
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.09, −0.13

Computer programs: COLLECT (Nonius, 1998), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXTL-Plus (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2ⁱ	0.82	2.02	2.798 (6)	158.2

Symmetry code: (i) −x+1, y−1/2, −z−1/2.

References

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Volume 64| Part 9| September 2008| Page o1835

doi:10.1107/S1600536808026998

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

(3S,4S,5S)-4-Hydr­­oxy-3-methyl-5-[(2S,3R)-3-methyl­pent-4-en-2-yl]-4,5-di­hydro­furan-2(3H)-one

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Experimental

Crystal data

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Supporting information

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organic compounds

(3S,4S,5S)-4-Hydroxy-3-methyl-5-[(2S,3R)-3-methylpent-4-en-2-yl]-4,5-dihydrofuran-2(3H)-one