Please use this identifier to cite or link to this item: http://nopr.niscair.res.in/handle/123456789/4550
Title: Synthesis of blocked trisaccharide analogue related to the repeating unit of the <i style="">O</i>-antigen form <i style="">E. coli</i> : 025
Authors: Srivastava, Jayant
Khare, Anakshi
Khare, Naveen K
Keywords: Carbohydrates
synthesis
regioselective
stereoselective
glycosylation
trisaccharide
Issue Date: Jun-2009
Publisher: CSIR
Abstract: <smarttagtype namespaceuri="urn:schemas-microsoft-com:office:smarttags" name="metricconverter"> Methyl 2-O-benzoyl-4, 6-O-benzylidene-O-<img src='/image/spc_char/alpha.gif'>-d-glucopyranoside <b style="">1 </b>was condensed with rhamnose-1-thio donor <b style="">2</b> in the presence of NIS/TMSOTf to yield the disaccharide<b style=""> </b>methyl 2,3,4-tri-O-acetyl-O-<img src='/image/spc_char/alpha.gif'>-l-rhamnopyranosyl-(1-3)-2-O-benzoyl-4,6-O-benzylidene-O-<img src='/image/spc_char/alpha.gif'>-d-glucopyranoside <b style="">3</b>.<b style=""> </b>Acidic hydrolysis of compound <b style="">3</b> followed by tritylation, deacylation and benzylation yields the disaccharide<b style=""> </b>methyl 2,3,4-tri-O-benzyl-O-<img src='/image/spc_char/alpha.gif'>-l-rhamnopyranosyl-(1-3)-2,4-di-O-benzyl-6-O-trityl-O-<img src='/image/spc_char/alpha.gif'>-d-glucopyranoside <b style="">6</b>. Compound <b style="">6</b> on detritylation yields the acceptor methyl 2,3,4-tri-O-benzyl-O-<img src='/image/spc_char/alpha.gif'>-l-rhamnopyranosyl-(1-3)-2,4-di-O-benzyl-O-<img src='/image/spc_char/alpha.gif'>-d-glucopyranoside <b style="">7 </b>which on condensation with known glucose-1-thio donorstyle <b>8</b> 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-<img src='/image/spc_char/alpha.gif'>-l-rhamnopyranosyl-(1-3)-2,4-di-O-benzyl-O-<img src='/image/spc_char/alpha.gif'>-d-glucopyranoside <b>9</b></smarttagtype>.
Description: 848-852
URI: http://hdl.handle.net/123456789/4550
ISSN: 0376-4699
Appears in Collections:IJC-B Vol.48B(06) [June 2009]

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