The total synthesis of C-glycosides with completely resolved seven-carbon backbone polyol stereochemistry: stereochemical correlations and access to L-configured and other rare carbohydrates.

Autor: Hoffmann HM; Department of Organic Chemistry, University of Hannover, Germany. hoffmann@mbox.oci.uni-hannover.de, Dunkel R, Mentzel M, Reuter H, Stark CB
Jazyk: angličtina
Zdroj: Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2001 Nov 19; Vol. 7 (22), pp. 4771-89.
DOI: 10.1002/1521-3765(20011119)7:22<4771::aid-chem4771>3.0.co;2-j
Abstrakt: The de novo synthesis of a full set of hydroxymethyl C-glycosides from only two precursors is described. The seven-carbon target molecules contain five stereocentres and bridge the stereochemical gap between natural D-configured and non-natural L-configured series of hexoses. Key steps include hydroxylation, differential protection, stereoselective reduction and desymmetrization of 8-oxabicyclo[3.2.1]oct-6-enes. C-Terminus differentiation and C-terminus excision of the seven-carbon polyol backbone lead to hexoses, including those of the L-series. A stereochemical and genetic classification of C-glycosides is presented.
Databáze: MEDLINE
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