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Crystal and molecular structure of the β-anomer of 6,7-dideoxy-1,2;3,4;9,10-tris-O-(1-methylethylidene)- d-erythro-α-d-galacto-undecopyranosid-8-ulose
Authors:Travis D. Weaver  Matthias Zeller  Peter Norris
Affiliation:(1) Department of Chemistry, Youngstown State University, One University Plaza, Youngstown,, OH 44555-3663, USA
Abstract:6,7-dideoxy-1,2;3,4;9,10-tris-O-(1-methylethylidene)-d-erythro-α-d-galacto-undecopy- ranosid-8-ulose, 3, was formed by adding a D-galactose-derived dithiane nucleophile to a protected erythronolactone followed by reductive removal of the dithioacetal group. Its β-anomer crystallizes in the chiral trigonal space group P3221 with a=b=12.2649(19) Å, c=24.675(8) Å, and Z=6. The molecule is composed of an erythrofuranose and a galactopyranose moiety, linked by a flexible ethylene bridge. The pyranose part of the molecule is disordered over two positions with equal occupancy. The configuration of the two disordered moieties is the same and they are converted into each other by a slight rotation of 6 degrees around one of the C–C single bonds of the ethylene bridge. The disorder allows for a more effective packing in the solid state.Supplementary material CCDC-602051 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif, by e-mailing data_request@ccdc.cam.ac.uk or by contacting The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44(0)1223-336033.
Keywords:C-glycosides  lactols  disorder
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