Synthesis of 2,3-di-O-glycosyl derivatives of methyl alpha- and beta-D-glucopyranoside.
The syntheses are described of 2,3-di-O-glycosyl derivatives of methyl alpha- and beta-D-glucopyranoside having alpha-D-manno-, beta-D-galacto-, alpha-L-rhamno-, alpha-L-fuco-, and beta-L-fuco-pyranosyl substituents at O-2 and O-3. The syntheses involved glycosylation of methyl 4,6-O-benzylidene-alpha- (24) and -beta-D-glucopyranoside (21), and substituted derivatives of 21 bearing 2-O-(2,3,4,6-tetra-O-benzoyl-alpha-D-mannopyranosyl)-, -(2,3,4,6-tetra-O- acetyl-beta-D-galactopyranosyl)-, -(2,3,4,-tri-O-benzoyl-alpha-L- rhamnopyranosyl)-, and -(2,3,4-tri-O-benzoyl-beta-L-fucopyranosyl) groups.
Nifant'ev
N E
NE
N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow.
Amochaeva VYu
Shashkov
A S
AS
Kochetkov
N K
NK
D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D005643:Fucose; D005690:Galactose; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008358:Mannose; D008757:Methylglucosides; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D012210:Rhamnose
D007202:Indicators and Reagents; D008757:Methylglucosides; D009844:Oligosaccharides; D005643:Fucose; D008358:Mannose; D012210:Rhamnose; D005690:Galactose