syn additions to 4alpha-epoxypyranosides: synthesis of L-idopyranosides.
The syn-selective addition of organozinc compounds to 4alpha-epoxypyranosides (4alpha-EPs), generated from methyl beta-D-glucoside or aminoglucoside, provides an efficient route to pyranosides with alpha-L-ido configurations, including L-iduronic acid, neosamine B, and higher monosaccharide derivatives.
Cheng
Gang
G
Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, IN 47907-2084, USA.
Fan
Renhua
R
Hernández-Torres
Jesús M
JM
Boulineau
Fabien P
FP
Wei
Alexander
A
D002241:Carbohydrates / Q000138:chemical synthesis* / Q000737:chemistry; D004852:Epoxy Compounds / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008745:Methylation; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism
D002241:Carbohydrates; D004852:Epoxy Compounds