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Reiterative Intramolecular Glycosylation Supported by a Rigid Spacer
Author(s) -
Paul Soumendu,
Müller Matthias,
Schmidt Richard R.
Publication year - 2003
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 - 10.1002/1099-0690(200301)2003:1<128::aid-ejoc128>3.0.co;2-s
Subject(s) - chemistry , intramolecular force , trisaccharide , disaccharide , glycosylation , stereochemistry , acceptor , combinatorial chemistry , biochemistry , physics , condensed matter physics
This paper describes a synthesis of trisaccharide 1 by reiterative intramolecular glycosidation with 5‐(bromomethyl)‐2‐methylbenzoic acid ( 5a ) as starting material for the generation of a rigid spacer. Intramolecular glycosidation of donor−acceptor‐tethered compound 24 yielded disaccharide 25 . Transesterification of 25 afforded 26 , which generated a new linking centre for the next spacer. Repetition of the previous cycle on 26 yielded trisaccharide 1 , which again presents an extension point for the synthesis of higher saccharides. (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2003)