REACTION OF MONOSACCHARIDE DERIVATIVES WITH STABILIZED SULFUR YLIDES - A HIGHLY STEREOSELECTIVE SYNTHESIS FOR C-GLYCOFURANOSIDES

Authors
VALPUESTA M DURANTE P LOPEZHERRERA FJ
Citation
M. Valpuesta et al., REACTION OF MONOSACCHARIDE DERIVATIVES WITH STABILIZED SULFUR YLIDES - A HIGHLY STEREOSELECTIVE SYNTHESIS FOR C-GLYCOFURANOSIDES, Tetrahedron, 49(42), 1993, pp. 9547-9560
Citations number
12
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
49
Issue
42
Year of publication
1993
Pages
9547 - 9560
Database
ISI
SICI code
0040-4020(1993)49:42<9547:ROMDWS>2.0.ZU;2-7
Abstract
Stereoselectivity in the formation of glycidic amides by reaction of v arious aldehydo- and keto-sugars [(1), (4), (6), (8), (10) and (12)] w ith N,N-dimethyl-2-(dimethylsulfuranylidene)acetamide (2) was studied. The reaction with derivatives of reducing cyclohemiacetalic monosacch arides (14) and (21), gives to alpha-C-glycofuranosyl-2(S)-hydroxyacet amides with a higher yield and stereoselectivity.