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Indian Journal of Chemistry -Section B (IJC-B) >
IJC-B Vol.44B [2005] >
IJC-B Vol.44B(01) [January 2005] >
| 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) |
| Source: | IJC-B Vol.44B(01) [January 2005]
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