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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

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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.

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Acknowledgments

MZ was supported by NSF grant 0111511, and the diffractometer was funded by NSF grant 0087210, by Ohio Board of Regents grant CAP-491, and by YSU. PN and TW were supported by a Cottrell College Science Award from Research Corporation (CC5400) as well as the National Institutes of Health (R15AI053112-01).

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  1. Department of Chemistry, Youngstown State University, One University Plaza, Youngstown,, OH, 44555-3663, USA

    Travis D. Weaver, Matthias Zeller & Peter Norris

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  1. Travis D. Weaver
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  2. Matthias Zeller
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Correspondence to Matthias Zeller.

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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.

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Weaver, T.D., Zeller, M. & Norris, P. 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. J Chem Crystallogr 36, 647–654 (2006). https://doi.org/10.1007/s10870-006-9112-6

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