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Solvent Effect in the Synthesis of Sialosyl α(2–6) Galactosides: Is Acetonitrile the only Choice?
Author(s) -
De Meo Cristina,
Farris Michael,
Ginder Nathan,
Gulley Bonnie,
Priyadarshani Uvege,
Woods Matthew
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.200800278
Subject(s) - chemistry , tetrahydrofuran , dichloromethane , acetonitrile , solvent , galactosides , organic chemistry , combinatorial chemistry , stereochemistry , glycoside
In spite of notable achievements for the synthesis of α‐sialosides that have been made in the past decades, sialylation reactions often require low temperatures (–40 to –78 °C) and the use of acetonitrile as a solvent. Herein we report that a C‐5 oxazolidinone sialosyl donor gives high yields andstereoselectivities in the presence of dichloromethane and/or tetrahydrofuran at 0 °C. Surprisingly, high stereoselectivities and yields are obtained even at ambient temperature in tetrahydrofuran.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)