3,4-O-(2,3-Dimethoxy­butane-2,3-di­yl)-S-(4-methyl­phen­yl)-1-thia-α-d-manno­pyran­oside

Fei-Fei Xu; Dong Han; Lin-Na Wang; Xiang-Bao Meng; Zhong-Jun Li

doi:10.1107/S1600536808018874

. 2008 Jun 28;64(Pt 7):o1367. doi: 10.1107/S1600536808018874

3,4-O-(2,3-Dimethoxybutane-2,3-diyl)-S-(4-methylphenyl)-1-thia-α-d-mannopyranoside

Fei-Fei Xu ^a, Dong Han ^a, Lin-Na Wang ^a, Xiang-Bao Meng ^a, Zhong-Jun Li ^a,^b,^*

PMCID: PMC2961734 PMID: 21202985

Abstract

In the title molecule, C₁₉H₂₈O₇S, the six-membered mannopyranoside and dioxane rings both display typical chair conformations. In the crystal structure, the hydroxy groups are involved in intermolecular hydrogen bonds, which link the molecules into chains extended along the b axis.

Related literature

For details of the synthesis, see Crich et al. (2000 ▶).

Experimental

Crystal data

C₁₉H₂₈O₇S
M _r = 400.47
Monoclinic,
a = 9.8272 (6) Å
b = 10.3152 (6) Å
c = 10.2585 (6) Å
β = 100.452 (3)°
V = 1022.64 (10) Å³
Z = 2
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 113 (2) K
0.32 × 0.26 × 0.18 mm

Data collection

Rigaku Saturn diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T _min = 0.940, T _max = 0.966
11384 measured reflections
4843 independent reflections
4168 reflections with I > 2σ(I)
R _int = 0.036

Refinement

R[F ² > 2σ(F ²)] = 0.034
wR(F ²) = 0.099
S = 1.08
4843 reflections
257 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.22 e Å⁻³
Absolute structure: Flack (1983 ▶), 2274 Friedel pairs
Flack parameter: 0.00 (9)

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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: CrystalStructure (Rigaku/MSC, 2005 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808018874/cv2406sup1.cif

e-64-o1367-sup1.cif^{(22.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808018874/cv2406Isup2.hkl

e-64-o1367-Isup2.hkl^{(237.2KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O5ⁱ	0.86 (3)	1.96 (3)	2.788 (2)	161 (2)
O5—H5⋯O7ⁱⁱ	0.80 (2)	2.21 (3)	2.971 (2)	158 (3)

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

We acknowledge financial support from the National Natural Science Foundation of China.

supplementary crystallographic information

Comment

The skeleton of the title compound, (I) (Figure 1), is a derivative of mannopyranoside and consists of a benzene ring and a bridged ring. Both of the six-membered mannopyranoside ring and the dioxane ring display a typical chair conformation. The two methoxy groups lie in axial bonds of the dioxane ring. The hydroxy groups are involved in the intermolecular hydrogen bonds (Table 1), which link the molecules into chains extended along b axis.

Experimental

The title compound was synthesized according to the known procedure (Crich et al., 2000). It was obtained from 4-methylphenyl-1-thio-alpha-D-mannopyranoside, and then dissolved in dry methanol followed by addition of butane-2,3-dione, HC(OMe)₃, and camphor-10-sulfonic acid. The reaction mixture was then heated to reflux for 72 h before it was cooled to room temperature and quenched by addition of Et₃N. The reaction mixture was concentrated under vacuum, after column chromatography(hexane-ethyl acetate 1:1) yield 78% as a white solid. The compound was crystallized from hexane-ethyl acetate(1:1) to yield colourless block-like crystals after a week at room temperature.