Synthesis of mono- and dihydroxylated furanoses, pyranoses, and an oxepanose for the preparation of natural product analogue libraries.
[structures: see text] Numerous biologically active natural products contain furanoses and pyranoses with mono- and dihydroxylated substituents. However, much of the structure-activity studies on such molecules is gathered on the aglycons without attention to the corresponding carbohydrate components. Consequently, there are few synthetic procedures that enable the rapid preparation of mono- and dihydroxyfuranoses and mono- and dihydroxypyranoses and no report for a 3,4-dihydroxyoxepanose. In this article we report the practical synthesis of orthogonally protected five-, six-, and seven-membered carbohydrate derivatives. The succinct manner in which these molecules were synthesized allows the rapid preparation of analogues aimed at discovering the role of ring size and individual hydroxyl moieties on the pyranose skeleton.
Department of Medicinal Chemistry and The Center for Protein Structure and Function, The University of Kansas, 1251 Wescoe Hall Dr., Malott Hall 4070, Lawrence, Kansas 66045-7564, USA.
Xiao Ming
XM
Yu
Huijong
H
Han
Brian S J
BS
Blagg
D001685:Biological Factors / Q000138:chemical synthesis*; D006027:Glycosides / Q000138:chemical synthesis; D015394:Molecular Structure; D009005:Monosaccharides / Q000138:chemical synthesis*; D013237:Stereoisomerism
D001685:Biological Factors; D006027:Glycosides; D009005:Monosaccharides