Convenient preparation of α- and β-glycosides of novel isomeric 3-deoxy-hept-2-ulosaric acids diesters

Methyl 3-deoxy-α and β- d- ribo, d- lyxo-hept-2-ulosonic acids were obtained from the individual α and β anomers of the same methyl (methyl 3-deoxy- d- arabino-hept-2-ulopyranosid)-onate in a sequential epimerisation at C-4 and/or C-5 of their appropriate O-trifluoromethanesulfonic derivatives, usin...

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Bibliographic Details
Published in:Tetrahedron 1997-07, Vol.53 (30), p.10643-10658
Main Authors: Mlynarski, Jacek, Banaszek, Anna
Format: Article
Language:English
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Summary:Methyl 3-deoxy-α and β- d- ribo, d- lyxo-hept-2-ulosonic acids were obtained from the individual α and β anomers of the same methyl (methyl 3-deoxy- d- arabino-hept-2-ulopyranosid)-onate in a sequential epimerisation at C-4 and/or C-5 of their appropriate O-trifluoromethanesulfonic derivatives, using cesium acetate. Subsequent oxidation of the 7-OH group in these compounds lead to the new isomeric 3-deoxy-hept-2-ulosaric acids derivatives. A convenient method for the preparation of the anomeric pairs of all isomeric 3-deoxy-hept-2-ulosonic acids, which allow their conversion to heptulosaric counterparts is reported.
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(97)00675-3