1,5-Anhydro-3,6-di-O-benzyl-2-deoxy-1,2-C-dichloromethylene-D-glycero-D-gulo-hexitol

Henok H Kinfe,Alfred Muller,Blessing A Aderibigbe

doi:10.1107/s1600536811040815

Abstract

In the title compound, C21H22Cl2O4, the pyranosyl ring adopts a twist-boat conformation with the O-benzyl groups in equatorial positions. In the crystal, O—H⋯O hydrogen bonding results in infinite chains of molecules along [100]. The structure is further consolidated by weak C—H⋯O, C—H⋯Cl and C—H⋯π interactions. The absolute structure was determined.

Highlights

In the title compound, C21H22Cl2O4, the pyranosyl ring adopts a twist-boat conformation with the O-benzyl groups in equatorial positions
The structure is further consolidated by weak C—HÁ Á ÁO, C— HÁ Á ÁCl and C—HÁ Á Á interactions
Cg1 and Cg2 are the centroids of the C1–C7 and C17–C22 rings, respectively

Summary

Structure Reports Online

Key indicators: single-crystal X-ray study; T = 100 K; mean (C–C) = 0.002 A; R factor = 0.023; wR factor = 0.055; data-to-parameter ratio = 13.2. C21H22Cl2O4, the pyranosyl ring adopts a twist-boat conformation with the O-benzyl groups in equatorial positions. O—HÁ Á ÁO hydrogen bonding results in infinite chains of molecules along [100]. The structure is further consolidated by weak C—HÁ Á ÁO, C— HÁ Á ÁCl and C—HÁ Á Á interactions. Related literature For O-benzyl deprotection methodologies, see: Akiyama et al (1991). See: Shanmugasundaram et al (2002). See: Cremer & Pople (1975)

Data collection

DÁ Á ÁA

Incoatec Quazar Multilayer Mirror monochromator

Special details