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Cascade Rearrangements of Polyunsaturated Sugars: A Novel Approach to the Synthesis of Oligosaccharide Mimetics
Author(s) -
Pearce Alan J.,
Chevalier Reynald,
Mallet JeanMaurice,
Sinaÿ Pierre
Publication year - 2000
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(200006)2000:12<2203::aid-ejoc2203>3.0.co;2-#
Subject(s) - chemistry , cascade , oligosaccharide , stereochemistry , combinatorial chemistry , organic chemistry , chromatography
The readily available tri‐unsaturated trisaccharide 4 undergoes a stereoselective cascade of reductive rearrangements with TIBAL (triisobutylaluminium) to afford, after oxidative workup, the (1→4) ether‐linked trisaccharide mimetics 3 and 10 .