Acetylated methyl glucopyranuronate trichloroacetimidate as a glycosyl donor for efficient synthesis of disaccharides.
Allyl (methyl 2,3,4-tri-O-acetyl-beta-D-glucopyranosyl uronate)-(1-->3)-4,6-O-benzylidene-2-deoxy-2-phthalimido-beta-D-glucopyranoside (4) and benzyl (methyl 2,3,4-tri-O-acetyl-beta-D-glucopyranosyl uronate)-(1-->3)-4,6-O-benzylidene-2-deoxy-2-phthalimido-beta-D-glucopyranoside (5) have been efficiently synthesized by coupling allyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-beta-D-glucopyranoside (2) or benzyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-beta-D-glucopyranoside (3) with methyl (2,3,4-tri-O-acetyl-1-O-trichloroacetimidoyl)-alpha-D-glucopyranuronate (1), respectively, using trimethylsilyl triflate as promoter.
Soliman
Sameh E
SE
Department of Chemistry, Faculty of Science, University of Alexandria, Ibrahemia, PO Box 426, Alexandria 21321, Egypt.
Bassily
Rafik W
RW
El-Sokkary
Ramadan I
RI
Nashed
Mina A
MA
D000107:Acetylation; D002855:Chromatography, Thin Layer; D004187:Disaccharides / Q000138:chemical synthesis* / Q000737:chemistry*; D005965:Glucuronates / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015394:Molecular Structure
D004187:Disaccharides; D005965:Glucuronates; D007097:Imines; C487457:methyl (2,3,4-tri-O-acetyl-1-O-trichloroacetimidoyl)glucopyranuronate