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Solid‐Phase Synthesis of Complex Oligosaccharides Using Azidoglucose as a Glycosyl Acceptor
Author(s) -
Wu Xiangyang,
Schmidt Richard R.
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.200400111
Subject(s) - chemistry , glycosyl , linker , solid phase synthesis , residue (chemistry) , regioselectivity , oligosaccharide , carbohydrate synthesis , glucosamine , combinatorial chemistry , stereochemistry , organic chemistry , polymer chemistry , carbohydrate , catalysis , biochemistry , peptide , computer science , operating system
The solid phase synthesis of oligosaccharides 1−3 was performed on Merrifield resin. These syntheses are based on the hydroxymethylbenzyl benzoate spacer‐linker system and, for regioselective chain extension, the use of O ‐glycosyl trichloroacetimidates as glycosyl donors containing temporary O ‐Fmoc protection. The important lactosamine‐containing oligosaccharides 1−3 are accessible in excellent yields by using a 2‐azidoglucose residue as the glucosamine building block adjacent to the spacer‐linker system. Only standard amounts of the glycosyl donor are employed in this solid phase oligosaccharide synthesis and we did not have to resort to any capping procedures. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)