6-Methyl-2-pyridyl N-acetyl-1-thio-β-d-glucosa­minide methanol monosolvate

Bo Chen; Miao Guo; Wei-Hua Jin; Yan-Wei Wang; Hong-Ze Liang

doi:10.1107/S1600536810036238

. 2010 Sep 15;66(Pt 10):o2561. doi: 10.1107/S1600536810036238

6-Methyl-2-pyridyl N-acetyl-1-thio-β-d-glucosaminide methanol monosolvate

Bo Chen ^a, Miao Guo ^a, Wei-Hua Jin ^a, Yan-Wei Wang ^a, Hong-Ze Liang ^a,^*

PMCID: PMC2983228 PMID: 21587547

Abstract

In the title compound, C₁₄H₂₀N₂O₅S·CH₄O, the pyranose and pyridine rings are linked through an S atom. The pyranose ring has a normal chair conformation. An intramolecular O—H⋯N hydrogen bond occurs. Intermolecular O—H⋯O, N—H⋯O, O—H⋯N and weak C—H⋯O hydrogen bonding is present in the crystal structure.

Related literature

For applications of glucopyranosides, see: Ashry et al. (2006 ▶). For the structure of an α-d-glucosaminide, see: Harrison et al. (2007 ▶).

Experimental

Crystal data

C₁₄H₂₀N₂O₅S·CH₄O
M _r = 360.42
Orthorhombic,
a = 7.3841 (15) Å
b = 14.041 (3) Å
c = 17.038 (4) Å
V = 1766.5 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 296 K
0.51 × 0.27 × 0.2 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T _min = 0.932, T _max = 0.950
12687 measured reflections
3173 independent reflections
2997 reflections with I > 2σ(I)
R _int = 0.161

Refinement

R[F ² > 2σ(F ²)] = 0.066
wR(F ²) = 0.170
S = 1.05
3173 reflections
222 parameters
H-atom parameters constrained
Δρ_max = 0.56 e Å⁻³
Δρ_min = −0.70 e Å⁻³
Absolute structure: Flack (1983 ▶), 1334 Fiedel pairs
Flack parameter: 0.01 (12)

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810036238/xu5024sup1.cif

e-66-o2561-sup1.cif^{(19KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810036238/xu5024Isup2.hkl

e-66-o2561-Isup2.hkl^{(152.5KB, 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
N1—H1A⋯O2ⁱ	0.86	2.15	2.925 (4)	149
O2—H2A⋯O3ⁱⁱ	0.82	2.02	2.794 (3)	156
O3—H3A⋯O4ⁱⁱ	0.82	1.88	2.646 (3)	155
O4—H4A⋯O6ⁱⁱⁱ	0.82	1.82	2.637 (4)	176
O6—H6⋯N2	0.82	1.98	2.795 (4)	175
C8—H8A⋯O5^iv	0.93	2.48	3.329 (4)	151
C12—H12C⋯O1^v	0.96	2.58	3.520 (4)	165
C15—H15C⋯O3^vi	0.96	2.56	3.367 (5)	142

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .

Acknowledgments

This project was sponsored by the Cultivation Program of Young and Middle-aged Academic Leaders in Zhejiang Higher Education Institutions, the Natural Science Foundation of Ningbo City (Nos. 2009 A610047 and 2010 A610027) and the K. C. Wong Magna Fund of Ningbo University. We thank Professor X. Li for help with the structural analysis.

supplementary crystallographic information

Comment

Thioglycosides are widely employed as biological inhibitors, glycosyl donors and enzyme resistant ligands for affinity chromatography (Ashry et al., 2006). Here we report the crystal structure of the title compound (Scheme 1). The title compound crystallizes exclusively as the β anomer. The molecule contains a pyranose ring and a pyridine ring linked by a sulfur atom. The pyranose ring has a normal chair conformation, similar to that found in an α-D-glucosaminide (Harrison et al. 2007). The extensive hydrogen bonding network is present in the crystal structure, involving O—H···O, O—H···N and N—H···O hydrogen bonding (Table 1). Weak intermolecular C—H···O hydrogen bonding is also present in the crystal structure.

Experimental

6'-Methyl-2'-pyridyl-2,3,4,6-tetraacetyl-1-thio-β-D-glucosaminide (1.5 g, 3.3 mmol) was dissolved in MeOH (10 ml) and one equivalent MeONa was added. The process of deacetylation was monitored by ¹H NMR. After removal of the solvent, the solid residue was washed with ethanol and ether, and then crystallized from H₂O/MeOH to give the title compound (0.23 g) as colorless crystals.