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Title: Synthesis of blocked trisaccharide analogue related to the repeating unit of the O-antigen form E. coli : 025
Authors: Srivastava, Jayant
Khare, Anakshi
Khare, Naveen K
Keywords: Carbohydrates;synthesis;regioselective;stereoselective;glycosylation;trisaccharide
Issue Date: Jun-2009
Publisher: CSIR
Abstract:  Methyl 2-O-benzoyl-4, 6-O-benzylidene-O--d-glucopyranoside 1 was condensed with rhamnose-1-thio donor 2 in the presence of NIS/TMSOTf to yield the disaccharide methyl 2,3,4-tri-O-acetyl-O--l-rhamnopyranosyl-(1-3)-2-O-benzoyl-4,6-O-benzylidene-O--d-glucopyranoside 3. Acidic hydrolysis of compound 3 followed by tritylation, deacylation and benzylation yields the disaccharide methyl 2,3,4-tri-O-benzyl-O--l-rhamnopyranosyl-(1-3)-2,4-di-O-benzyl-6-O-trityl-O--d-glucopyranoside 6. Compound 6 on detritylation yields the acceptor methyl 2,3,4-tri-O-benzyl-O--l-rhamnopyranosyl-(1-3)-2,4-di-O-benzyl-O--d-glucopyranoside 7 which on condensation with known glucose-1-thio donorstyle 8 in the presence of NIS/TMSOTf yields the linear protected trisaccharide methyl 2,3,4,6-tetra-O-acetyl-O-β-d-glucopyranosyl-(1-6)-2,3,4-tri-O-benzyl-O--l-rhamnopyranosyl-(1-3)-2,4-di-O-benzyl-O--d-glucopyranoside 9.
Page(s): 848-852
ISSN: 0376-4699
Appears in Collections:IJC-B Vol.48B(06) [June 2009]

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