Syntheses of O-[beta]-D-Mannosyl-(1->4)-O-[alpha]-D-mannosyl-(1->3)-L-rhamnose and O-(2-Acetamido-2-deoxy-[beta]-D-mannosyl)-(1->4)-O-[alpha]-D-galactosyl-(1->4)-D-galactose via In-situ-activating Glycosylation Using 2-O-Acetyl-3,4,6-tri-O-benzyl-D-glucose

• Published in: Bulletin of the Chemical Society of Japan 2003-08, Vol.76 (8), p.1603
• Main Authors: Koto, Shinkiti, Shinoda, Yoshika, Hirooka, Motoko, Sekino, Akiko, Ishizumi, Sachiko, Koma, Mutsuko, Matuura, Chieko, Sakata, Naoko
• Format: Article
• Language: English
• ISSN: 0009-2673; 1348-0634

O-β-D-Mannopyranosyl-(1->4)-O-α-D-mannopyranosyl-(1->3)-L-rhamnopyranose, a trisaccharide including a repeating unit of the O-specific polysaccharide (OSP) of Bulkholderia vietnamiensis strain LMG 6988, and O-(2-acetamido-2-deoxy-β-D-mannopyranosyl)-(1->4)-O-α-D-galactopyranosyl-(1->4)-D-galactopyranose, a trisaccharide including a repeating unit of OSP of Acinetobactor baumannii serogroup O18, were synthesized by means of in-situ-activating glycosylation using 2-O-acetyl-3,4,6-tri-O-benzyl-D-glucopyranose (2ATBG) and a reagent mixture of p-nitrobenzenesulfonyl chloride, silver triflate, and 1,8-diazabicyclo[5.4.0]undec-7-ene, and related systems. New syntheses of 2ATBG, allyl 2,3,6-tri-O-benzyl-α-D-galactopyranoside, benzyl 2,3,6-tri-O-benzyl-α-D-galactopyranoside, and 2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-mannopyranose are described.