Phenyl 2-amino-N,6-O-dibenzyl-2,3-N,O-carbonyl-2-de­oxy-1-thio-β-d-glucopyran­oside

Shino Manabe; Kazuyuki Ishii; Daisuke Hashizume; Yukishige Ito

doi:10.1107/S1600536808027189

. 2008 Sep 6;64(Pt 10):o1868. doi: 10.1107/S1600536808027189

Phenyl 2-amino-N,6-O-dibenzyl-2,3-N,O-carbonyl-2-deoxy-1-thio-β-d-glucopyranoside

Shino Manabe ^a,^*, Kazuyuki Ishii ^a, Daisuke Hashizume ^b, Yukishige Ito ^a

PMCID: PMC2959351 PMID: 21201084

Abstract

In the crystal structure of the title compound, C₂₇H₂₇NO₅S, the pyranose ring adopts a ⁴ C ₁ chair conformation with puckering parameters Q = 0.639 (2) Å, θ = 174.11 (18) and ϕ = 256 (2)°. The presence of the 2,3-trans-oxazolidinone fixes the conformation of the pyranose ring. The phenyl group attached to the S atom and the benzyl group bonding to the N atom are each disordered over two positions with site occupancies of 0.624 (3):0.376 (3) and 0.526 (3):0.474 (3), respectively. An intermolecular O—H⋯O hydrogen bond is observed.

Related literature

For related literature, see: Benakli et al. (2001 ▶); Boysen et al. (2005 ▶); Cremer & Pople (1975 ▶); Crich & Vinod (2005 ▶); Geng et al. (2008 ▶); Manabe et al. (2006 ▶); Satoh et al. (2008 ▶).

Experimental

Crystal data

C₂₇H₂₇NO₅S
M _r = 477.56
Monoclinic,
a = 13.8166 (7) Å
b = 5.7008 (3) Å
c = 15.0425 (9) Å
β = 91.494 (4)°
V = 1184.43 (11) Å³
Z = 2
Mo Kα radiation
μ = 0.18 mm⁻¹
T = 90 K
0.30 × 0.08 × 0.07 mm

Data collection

Rigaku AFC8 diffractometer with Saturn70 CCD
Absorption correction: multi-scan (MULABS; Blessing, 1995 ▶) T _min = 0.959, T _max = 0.998
7074 measured reflections
4965 independent reflections
3970 reflections with I > 2σ(I)
R _int = 0.040

Refinement

R[F ² > 2σ(F ²)] = 0.058
wR(F ²) = 0.167
S = 1.03
4965 reflections
353 parameters
31 restraints
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.34 e Å⁻³
Absolute structure: Flack (1983 ▶), 1983 Friedel pairs
Flack parameter: 0.05 (11)

Data collection: CrystalClear SM (Rigaku/MSC, 2005 ▶); cell refinement: HKL-2000 (Otwinowski & Minor, 1997 ▶); data reduction: HKL-2000; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808027189/is2324sup1.cif

e-64-o1868-sup1.cif^{(29.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808027189/is2324Isup2.hkl

e-64-o1868-Isup2.hkl^{(243.1KB, 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
O3—H3O⋯O5ⁱ	0.84	1.98	2.774 (2)	158

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Symmetry code: (i) Inline graphic .

Acknowledgments

SM acknowledges an Incentive Research Grant from RIKEN and Grants-in Aid for Scientific Research for Scientific Research (C) from the Japan Society for the Promotion of Science (grant No. 19590032).

supplementary crystallographic information

Comment

Recently, we and other groups reported 2,3-trans-oxazolidinone carrying novel glycosyl donors for α-selective glycosylation (Benakli et al., 2001; Boysen et al., 2005; Crich & Vinod, 2005; Manabe et al., 2006; Geng et al., 2008). Furthermore, we also found the 2,3-trans-oxazolidinone carrying pyranoses are easily anomerized via an endo-cleavage manner (Manabe et al., 2006; Satoh et al., 2008). In order to investigate the origin of the high stereosetectivity and its unique character, we are interested in the conformation of the pyranose ring with 2,3-trans-oxazolidinone group.

The pyranose ring of the title compound adapts a ⁴C₁ chair conformation. The torsion angles (O1—C1—C2—C3, C1—C2—C3—C4, C2—C3—C4—C5, C3—C4—C5—O1, C4—C5—O1—C1 and C5—O1—C1—C2; see geometric parameters table in supplementary materials) and Cremer-Pople puckering parameters (Cremer & Pople, 1975), Q = 0.639 (2) Å, θ = 174.11 (18)° and φ = 256 (2)°, of the ring clearly indicate the ⁴C₁ conformation.

Experimental

The compound, (I), was prepared as described by Benakli et al. (2001). (I) was dissolved in ethyl acetate at room temperature and hexane was added. The solution was kept at room temperature in a sealed flask for a few days to give single crystals suitable for single-crystal X-ray analysis.