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Lipophilic Thioglycosides for the Solution‐Phase Synthesis of Oligosaccharides Using Biphasic Liquid‐Liquid Separation
Author(s) -
Encinas Lourdes,
Chiara Jose Luis
Publication year - 2009
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.200900081
Subject(s) - chemistry , anomer , liquid–liquid extraction , chromatography , extraction (chemistry) , oligosaccharide , organic chemistry , combinatorial chemistry , chemical polarity , molecule
A simple “heavy” lipophilic tag readily prepared from inexpensive gallic acid can greatly simplify the purification steps in oligosaccharide synthesis through liquid‐liquid extraction (LLE) using two immiscible organic solvents. By introducing the tag at the anomeric position of the carbohydrate acceptor, this simple LLE purification can be advantageously carried out at each step throughout the synthetic route. We have developed efficient tagging and detagging procedures and have shown that a single tag is sufficient to ensure a high affinity of the tagged molecule for alkane solvents even in the case of highly polar substrates.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)