STEREOSELECTIVE SYNTHESIS OF N-(ALPHA-RIBOFURANOSYL AND BETA-RIBOFURANOSYL)-FORMAMIDES AND RELATED GLYCOSYL FORMAMIDES - PRECURSORS FOR SUGAR ISOCYANIDES

Authors
EWING DF HIEBL J HUMBLE RW MACKENZIE G RAYNOR A ZBIRAL E
Citation
Df. Ewing et al., STEREOSELECTIVE SYNTHESIS OF N-(ALPHA-RIBOFURANOSYL AND BETA-RIBOFURANOSYL)-FORMAMIDES AND RELATED GLYCOSYL FORMAMIDES - PRECURSORS FOR SUGAR ISOCYANIDES, Journal of carbohydrate chemistry, 12(7), 1993, pp. 923-932
Citations number
16
Categorie Soggetti
Chemistry Inorganic & Nuclear",Biology
Journal title
Journal of carbohydrate chemistry → ACNP
ISSN journal
07328303
Volume
12
Issue
7
Year of publication
1993
Pages
923 - 932
Database
ISI
SICI code
0732-8303(1993)12:7<923:SSONAB>2.0.ZU;2-E
Abstract
Efficient stereospecific N-formylation of ribosylamine has been achiev ed, affording the alpha-anomer directly (by reaction with formic-aceti c anhydride) and the beta-anomer via the corresponding formamidine der ivative (by reaction with dimethylformamide dimethyl acetal). Dehydrat ion of the alpha-anomer gave the corresponding isocyanide without comp romising the anomeric purity. The amidine route was extended to give t he N-formyl derivatives of alpha-xylosylamine and alpha-arabinosylamin e.