First Intramolecular Aglycon Delivery onto a  D ‐Fucofuranosyl Entity for the Synthesis of α‐ D ‐Fucofuranose‐Containing Disaccharides | Zendy

Gelin Muriel | Zendy; Ferrières Vincent | Zendy; Lefeuvre Martine | Zendy; Plusquellec Daniel | Zendy

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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)

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