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Synthesis of Oligosaccharides Related to a Biodynamic Saponin from Calamus Insignis as Their Propargyl Glycosides
Author(s) -
Dasgupta Somnath,
Mukhopadhyay Balaram
Publication year - 2008
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200800834
Subject(s) - chemistry , glycoside , calamus , saponin , rhamnose , glycosylation , propargyl , carbohydrate , total synthesis , protecting group , glucuronic acid , organic chemistry , stereochemistry , polysaccharide , botany , biochemistry , catalysis , medicine , alternative medicine , alkyl , pathology , biology
The total synthesis of the carbohydrate portion (penta‐and tetrasaccharides) of steroidal saponins, isolated from Calamus insignis , is reported. A simple route is followed, starting from commercially available D ‐glucose and L ‐rhamnose, through high‐yielding protecting group manipulation strategies. Sulfuric acid immobilized on silica (H 2 SO 4 /silica) was used as an effective Brönsted acid source in conjunction with N ‐iodosuccinimide for activation of thioglycosides or alone for trichloroacetimidate donors in key glycosylation steps. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)