Please use this identifier to cite or link to this item: http://nopr.niscair.res.in/handle/123456789/8929
Title: Synthesis of tetrasaccharide related to the repeating unit of the <i>O</i>-antigen from <i>Shigella boydii </i>type 5 in the form of its <i>tert</i>-butyl ester and 2-(trimethylsilyl)ethyl glycoside
Authors: Roy, Samarpita
Sarkar, Sujit Kumar
Mukhopadhyay, Balaram
Roy, Nirmolendu
Issue Date: Jan-2005
Publisher: CSIR
Series/Report no.: <b>Int</b>.<b>Cl</b>.<b><sup>7</sup> C 07 H 3/06</b>
Abstract: Starting from D-mannose, D-glucose and L-rhamnose, two disaccharide blocks ethyl 2,3,4-tri-<i>O</i>-benzyl-<img src='/image/spc_char/alpha.gif' border=0> -L-rhamnopyranosyl-(1→3)-2-<i>O</i>-benzyl-4,6-<i>O</i>-benzylidene-1-thio-<img src='/image/spc_char/alpha.gif' border=0>-D-mannopyranoside and <i>tert-</i>butyl 2-<i>O</i>-benzyl-4,6-<i>O</i>-benzylidene-<img src='/image/spc_char/beta.gif' border=0>-D-mannopyranosyl-(1→4)-[2-(trimethylsilyl)ethyl 2,3-di-<i>O</i>-benzyl-<img src='/image/spc_char/beta.gif' border=0>-D-glucopyranosid]uronate have been synthesized. Schmidt’s inverse addition technique of trichloroacetimidate is utilized for the construction of a disaccharide with a <img src='/image/spc_char/beta.gif' border=0>-mannosidic linkage in good yield. Coupling of this two disaccharides give the desired tetrasaccharide derivative, <i>tert-</i>butyl 2,3,4-tri-<i>O</i>-benzyl-<img src='/image/spc_char/alpha.gif' border=0> -L-rhamnopyranosyl-(1→3)-2-<i>O</i>-benzyl-4,6-<i>O</i>-benzylidene-<img src='/image/spc_char/beta.gif' border=0>-D-mannopyranosyl-(1→3)-2-<i>O</i>-benzyl-4,6-<i>O</i>-benzylidene-<img src='/image/spc_char/beta.gif' border=0>-D-mannopyranosyl-(1→4)-[2-(trimethylsilyl)ethyl 2,3-di-<i>O</i>-benzyl-<img src='/image/spc_char/beta.gif' border=0>-D-glucopyranosid]­uronate, which is related to the repeating unit of <i>Shigella boydii</i> type 5. The tetrasaccharide can be coupled with a suitable protein for the preparation of a synthetic vaccine.
Description: 130-136
URI: http://hdl.handle.net/123456789/8929
ISSN: 0975-0983(Online); 0376-4699(Print)
Appears in Collections:IJC-B Vol.44B(01) [January 2005]

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