Alkylidenation of sugar lactones and further transformation to C-glycosides

Article abstract of DOI:10.1080/07328309908544013

The Wittig reaction of (carbethoxymethylene)triphenylphosphorane with perbenzylated sugar δ-lactones and their 2-acetamido-2-deoxy derivatives is described. It is shown that this olefination occurred readily with the galacto and gluco derivatives, leading stereoselectively to Z-C-glycosylidenes in good yields. However, the same reaction with the perbenzylated 2-deoxy-D-arabino-hexono-1,5-lactone and the mannonolactones worked poorly. Reduction over Pd/C followed by acetylation of the obtained C-glycosylidenes led stereoselectively to peracetylated β-C-glycosides and amino β-C-glycosides. The olefin function could also be reduced selectively by Raney nickel or NiCl₂/NaBH₄, affording the perbenzylated C-glycosides and amino β-C-glycosides. Other transformation of the enol ether function is also reported.

Full text of DOI:10.1080/07328309908544013

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Journal of Carbohydrate Chemistry
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Alkylidenation of Sugar Lactones
and Further Transformation to C-
Glycosides
Juan Xie , Adeline Molina & Stanislas Czernecki
a Laboratoire de Chimie des Glucides, CNRS UMR 7613 ,
Université Pierre et Marie Curie , 4 Place Jussieu, 75005
Paris, FRANCE
b Laboratoire de Chimie des Glucides, CNRS UMR 7613 ,
Université Pierre et Marie Curie , 4 Place Jussieu, 75005
Paris, FRANCE
c Laboratoire de Chimie des Glucides, CNRS UMR 7613 ,
Université Pierre et Marie Curie , 4 Place Jussieu, 75005
Paris, FRANCE
Published online: 27 Feb 2008.
To cite this article: Juan Xie , Adeline Molina & Stanislas Czernecki (1999) Alkylidenation
of Sugar Lactones and Further Transformation to C-Glycosides, Journal of Carbohydrate
Chemistry, 18:5, 481-498, DOI: 10.1080/07328309908544013
To link to this article: http://dx.doi.org/10.1080/07328309908544013
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