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Synthesis of the tetrasaccharide repeating-unit of the polysaccharide from Klebsiella type 23

✍ Scribed by Asim K. Ray; Nirmolendu Roy

Publisher
Elsevier Science
Year
1990
Tongue
English
Weight
450 KB
Volume
196
Category
Article
ISSN
0008-6215

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✦ Synopsis

Methyl 2-0-allyl-4-O-benzyl-3-0-(2,3,4,6-tetra-O-acetyl-~-D-glucopyranosyl)-cx-L-rhamnospyranoside was obtained by condensing methyl 2-O-allyl-4-O-benzyl-a+rhamnopyranoside with tetra-O-aCetyl-cr-D-glUCOp~anOSy1 bromide. Benzylation, removal of the ally1 group, and condensation of the product with ethyl 6-0-acetyl-2,3,4-tri-O-benzyl-l-thio-B-D-glucopyranoside gave methyl 2-0-(6-0acetyl-2,3,4-tri-O-benzyl-cY-D-glucopyranosyl)-4-O-benzyl-3-O-(2,3,4,6-tetra-Obenzyl-P-o-glucopyranosyl)-cr-r_-rhamnopyranoside. 0-Deacetylation, condensation of the product with methyl (2,3,4-tri-0-acetyl-cu-o-glucopyranosyl bromide)uronate, and removal of the protecting groups gave methyl 3-0-/3-D-glucopyranosyl-2-O-[6-O-(/3-D-glucopyranosyluronic acid)-cu-D-glucopyranosyl]-cu-L-rhamnopyranoside (13).

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