Stereoselective epoxidation of alkenylidene acetals derived from carbohydrates with d- allo, d- altro, d- galacto, d- gluco and d- xylo configurations

The synthesis of 2,3-epoxypropylidene acetals of sugar derivatives from N-acetyl-2-amino-2-deoxy- d-allopyranose, d-altropyranose, d-galactopyranose, N-acetyl- d-glucosamine, d-glucofuranose and d-xylofuranose is described. The epoxidation with m-CPBA of the corresponding alkenylidene derivatives to...

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Bibliographic Details
Published inTetrahedron: asymmetry Vol. 18; no. 15; pp. 1850 - 1867
Main Authors Vega-Pérez, José M., Vega, Margarita, Blanco, Eugenia, Iglesias-Guerra, Fernando
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 09.08.2007
Elsevier
Subjects
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Chemistry, Physical
Physical Sciences
Science & Technology
OXAZOLIDINES
POTENTIAL ANTICANCER DRUGS
D-GLUCOSAMINE
ALKYLATING-AGENTS
PART 6
2-AMINO-2-DEOXY-D-ALLOSE
ASYMMETRIC EPOXIDATION
CHIRAL AUXILIARIES
SUGARS
DERIVATIVES
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Summary:The synthesis of 2,3-epoxypropylidene acetals of sugar derivatives from N-acetyl-2-amino-2-deoxy- d-allopyranose, d-altropyranose, d-galactopyranose, N-acetyl- d-glucosamine, d-glucofuranose and d-xylofuranose is described. The epoxidation with m-CPBA of the corresponding alkenylidene derivatives took place with different stereoselectivities depending upon the sugar configuration, the protecting group of the hydroxyl groups of the sugar, and the substitution of the unsaturated system. The analysis of the ring-opening reaction of these oxiranes by hydrogenolysis enabled the assignation of their configuration at the new stereogenic centres.
ISSN:0957-4166
1362-511X
DOI:10.1016/j.tetasy.2007.07.015