Please use this identifier to cite or link to this item:
|Title: ||Synthesis of blocked trisaccharide analogue related to the repeating unit of the O-antigen form E. coli : 025|
|Authors: ||Srivastava, Jayant|
Khare, Naveen K
|Issue Date: ||Jun-2009|
|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.|
|Appears in Collections:||IJC-B Vol.48B(06) [June 2009]|
Items in NOPR are protected by copyright, with all rights reserved, unless otherwise indicated.