Crystal structures of two new anomeric 2,3-unsaturated C-glycopyranosides

Jan C.A. Boeyens, S. Don Travlos, Gerhard J. Engelbrecht, Cedric W. Holzapfel, Gert J. Kruger

Research output: Contribution to journalArticlepeer-review

Abstract

The crystal structures of isopropylidene [4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-eno-pyranosyl]- methylmalonate 1 and its β-anomer 2 have been determined by single-crystal X-ray diffraction. Both compounds crystallize with space group P21 and cell constants of 1: a, b, c = 10.635 (1), 8.102 (2), 11.212 (1)° β = 107.20 (1)° and 2: a, b, c = 9.995 (1), 10.230 (1), 10.105 (1) Å; β = 115.71 (1)°. The two compounds differ in stereochemistry only at the 1-position which confirms previous conclusions based on nmr spectroscopy. The cyclic fragments in the structures all have related conformations, close to envelope forms. The results confirm that Pd-catalyzed allylic substi-tution proceeds largely with retention of configuration.

Original languageEnglish
Pages (from-to)48-51
Number of pages4
JournalSouth African Journal of Chemistry
Volume50
Issue number1
Publication statusPublished - Mar 1997

ASJC Scopus subject areas

  • General Chemistry

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