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Title: Synthesis of tetrasaccharide related to the repeating unit of the O-antigen from Shigella boydii type 5 in the form of its tert-butyl ester and 2-(trimethylsilyl)ethyl glycoside
Authors: Roy, Samarpita
Sarkar, Sujit Kumar
Mukhopadhyay, Balaram
Roy, Nirmolendu
Issue Date: Jan-2005
Publisher: CSIR
IPC Code: Int.Cl.7 C 07 H 3/06
Abstract: Starting from D-mannose, D-glucose and L-rhamnose, two disaccharide blocks ethyl 2,3,4-tri-O-benzyl- -L-rhamnopyranosyl-(1→3)-2-O-benzyl-4,6-O-benzylidene-1-thio--D-mannopyranoside and tert-butyl 2-O-benzyl-4,6-O-benzylidene--D-mannopyranosyl-(1→4)-[2-(trimethylsilyl)ethyl 2,3-di-O-benzyl--D-glucopyranosid]uronate have been synthesized. Schmidt’s inverse addition technique of trichloroacetimidate is utilized for the construction of a disaccharide with a -mannosidic linkage in good yield. Coupling of this two disaccharides give the desired tetrasaccharide derivative, tert-butyl 2,3,4-tri-O-benzyl- -L-rhamnopyranosyl-(1→3)-2-O-benzyl-4,6-O-benzylidene--D-mannopyranosyl-(1→3)-2-O-benzyl-4,6-O-benzylidene--D-mannopyranosyl-(1→4)-[2-(trimethylsilyl)ethyl 2,3-di-O-benzyl--D-glucopyranosid]­uronate, which is related to the repeating unit of Shigella boydii type 5. The tetrasaccharide can be coupled with a suitable protein for the preparation of a synthetic vaccine.
Page(s): 130-136
ISSN: 0975-0983(Online); 0376-4699(Print)
Appears in Collections:IJC-B Vol.44B(01) [January 2005]

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