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Synthesis 1995; 1995(5): 561-565
DOI: 10.1055/s-1995-3955
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Application of Ortho Esterification under Kinetically Controlled Conditions to the Selective Acylation in the D-Gluco-, D-Ribo- and D-Xylo-furanose Series

Mohamed Bouchra* , Pierre Calinaud1 , Jacques Gelas1
  • *Ecole Nationale Supérieure de Chimie de Clermont-Ferrand, B.P. 187 F-63174 Aubière, France, Fax +33(73)407095
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Publikationsdatum:
31. Dezember 2000 (online)

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The ortho esterification of various glucofuranoses in the D-ribo-, D-xylo and D-gluco series under kinetic control was obtained through the action of 1,1-dimethoxyethene (a ketene acetal) on the monosaccharide using mild acid conditions. The selective hydrolysis of the methoxyethylidene derivatives thus obtained, gave access to α-hydroxy acetates which are useful synthetic intermediates.

carbohydrates - orthoesters - acetals - acylation