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Synthesis of a New Type of Glycosidic Linkage: Acetal‐Linked Disaccharides and Trisaccharides of Acyclic and Cyclic Sugars
Author(s) -
Madhusudan Soni Kamlesh,
Misra Anup Kumar
Publication year - 2005
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.200500081
Subject(s) - chemistry , trisaccharide , glycosidic bond , acetal , stereochemistry , sugar , organic chemistry , enzyme
New types of di‐ and trisaccharides related to a unique trisaccharide present in the cell walls of Proteus have been synthesized by coupling of acyclic sugar dithioacetals and di‐ and monohydroxy cyclic sugars. In this class of compounds an acyclic sugar is linked to a cyclic sugar through an acetal linkage. The formation of these acetal‐linked pseudodi‐ and‐trisaccharides has been achieved by a generalized reaction procedure mediated by 1,3‐dibromo‐5,5‐dimethylhydantoin under mild, metal‐free and neutral conditions. Sixteen protected and twelve deprotected di‐ and trisaccharides related to the trisaccharide found in the Proteus cell wall have been synthesized. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)