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Synthesis of Thioglycosides by Tetrathiomolybdate‐Mediated Michael Additions of Masked Thiolates
Author(s) -
Sridhar Perali Ramu,
Prabhu Kandikere Ramaiah,
Chandrasekaran Srinivasan
Publication year - 2004
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.200400360
Subject(s) - chemistry , reagent , intramolecular force , michael reaction , halide , sulfur , combinatorial chemistry , ammonium , organic chemistry , aqueous solution , catalysis
An efficient one‐pot methodology for the synthesis of thioglycosides in excellent yields under neutral conditions through the use of benzyltriethylammonium tetrathiomolybdate [(BnNEt 3 ) 2 MoS 4 ; 1 ] as a sulfur‐transfer reagent has been developed. The reagent 1 reacts with sugar halides to give sugar disulfides, which then undergo reductive cleavage in situ to provide the corresponding thiolates, followed by Michael addition to give the corresponding thioglycosides. Further, the utility of this one‐pot reaction in aqueous medium has been exemplified through the use of ammonium tetrathiomolybdate [(NH 4 ) 2 MoS 4 ; 2 ]. The application of this methodology has been extended to the synthesis of a variety of thiosugar analogues with excellent diastereoselectivity through inter‐ and intramolecular reactions. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)