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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 32, 2002 - Issue 19
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Original Articles

BIS-DESULFOGLUCOSINOLATES: A NEW CLASS OF BOLAFORMS

Dominique Lafont Laboratoire de Chimie Organique II, Université Lyon I, UMR 5622 CNRS, Bât 308, 43 Bd du 11 Novembre 1918, Villeurbanne Cedex, 69622, FranceCorrespondence[email protected]
,
Yves Chevalier Laboratoire des Matériaux Organiques à Propriétés Spécifiques, UPR 9031 CNRS, Vernaison, 69390, France
,
Valérie Grumel ICOA, Université d'Orléans, UPRES-A 6005, B.P. 6759, Orléans Cedex 2, F-45067, France
,
Stéphanie Cassel ICOA, Université d'Orléans, UPRES-A 6005, B.P. 6759, Orléans Cedex 2, F-45067, France
&
Patrick Rollin ICOA, Université d'Orléans, UPRES-A 6005, B.P. 6759, Orléans Cedex 2, F-45067, France
Pages 2919-2930 | Received 27 Sep 2001, Published online: 16 Aug 2006
 
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ABSTRACT

Bis-desulfoglucosinolates 14–18 bearing d-gluco, lacto, malto and cellobio saccharidic moieties were synthesized in two steps from the corresponding protected 1-thio-β-d-glycopyranoses 5, 8, 10 and 12 and bis-hydroximoyl chlorides 3a and 4a derived from 1,8-octanedial (1) and 1,12-dodecanedial (2). Fully deprotections of the intermediate O-acetylated derivatives 6, 7, 9, 11 and 13 were realized either using Zemplén method or methanol/triethylamine/water mixture, the choice of the conditions being dependent on the solubility in methanol of the fully and partially acetylated derivatives.

ACKNOWLEDGMENT

Dr. Bruno Perly (SCM, CEA Saclay, France) is gratefully acknowledged for competent NMR assistance.

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