223546-30-3Relevant academic research and scientific papers
Benzyl derivatives of N-2,4-dinitrophenyl-D-glucosamine and their use for oligosaccharide synthesis
Koto, Shinkiti,Hirooka, Motoko,Yago, Kazuo,Komiya, Mitsuo,Shimizu, Toshio,Kato, Kumi,Takehara, Tsunehiko,Ikefuji, Ayami,Iwasa, Ayako,Hagino, Saho,Sekiya, Michiyo,Nakase, Yozo,Zen, Shonosuke,Tomonaga, Fumiya,Shimada, Shigehiko
, p. 173 - 183 (2007/10/03)
Four tri-O-benzyl derivatives of 2-deoxy-2-(2,4-dinitroanilino)-D- glucopyranose were synthesized. Glycosylation using 3,4,6-tri-O-benzyl-2- deoxy-2-(2,4-dinitroanilino)-D-glucopyranose as glycosyl donor and a reagent mixture of p-nitrobenzenesulfonyl chloride, silver trifluoromethanesulfonate, and triethylamine produced β-glycosides with complete selectivity. Starting from benzyl 3,6-di-O-benzyl-2-deoxy-2-(2,4-dinitroanilino)-β-D- glucopyranoside as acceptor, O-α-D-galactopyranosyl-(1 → 4)-O-β-D- galactopyranosyl-(1 → 4)-2-acetamido-2-deoxy-D-glucopyranose, the human blood-group P1-antigenic determinant, was synthesized.
Glycosylation using 2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-glucose, - galactose, and -mannose with the aid of p-nitrobenzenesulfonyl chloride- silver trifluoromethanesulfonate-triethylamine system
Koto, Shinkiti,Asami, Kazuyasu,Hirooka, Motoko,Nagura, Kazuo,Takizawa, Mizue,Yamamoto, Satoko,Okamoto, Nami,Sato, Mitsuko,Tajima, Hiromi,Yoshida, Toyosaku,Nonaka, Nobuo,Sato, Tadaaki,Zen, Shonosuke,Yago, Kazuo,Tomonaga, Fumiya
, p. 765 - 777 (2007/10/03)
This report describes a simple synthesis of 2-azido-3,4,6-tri-O-benzyl- 2-deoxy-D-glucopyranose. Glycosylation using this as well as 2-azido-3,4,6- tri-O-benzyl-2-deoxy-D-galactopyranose and -mannopyranose was achieved with the aid of a reagent system consisting of p-nitrobenzenesulfonyl chloride, silver trifluoromethanesulfonate, and triethylamine, and its modifications. O-(2-Acetamido-2-deoxy-β-D-glucopyranosyl)-(1 → 4)-O-α-D-mannopyranosyl- (1 → 4)-a-D-mannopyranose, the repeating unit of the main chain of the O- specific cell wall polysaccharide of E. coli 058 was synthesized.
