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First Intramolecular Aglycon Delivery onto a D ‐Fucofuranosyl Entity for the Synthesis of α‐ D ‐Fucofuranose‐Containing Disaccharides
Author(s) -
Gelin Muriel,
Ferrières Vincent,
Lefeuvre Martine,
Plusquellec Daniel
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/ejoc.200390184
Subject(s) - chemistry , intramolecular force , stereochemistry , catalysis , residue (chemistry) , organic chemistry
Intramolecular aglycon delivery was performed for the first time starting from n ‐pentenyl glycofuranoside as a donor. p ‐Methoxybenzyl‐assisted aglycon transfer required very mild reaction conditions and was promoted by N ‐iodosuccinimide without assistance of any Lewis acid catalyst. As a result, rare α‐ D ‐fucofuranose‐containing disaccharides were obtained. Moreover, structure elucidation led to the conclusion that an N ‐succinimidyl residue was still present in the resulting products. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)