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US 5,288,859 AGranted
Process for the preparation of glycosyl azides
AssigneeE. I. Du Pont de Nemours and Company
InventorSubramaniam Sabesan
Life of this patent
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Abstract
A process for stereospecific preparation of glycosyl azides by reacting a metal azide with a glycosyl phosphate triester having the phosphate group cis to the adjacent C-2 substituent is disclosed.
Claims10
A process for the stereospecific preparation of a glycosyl azide of Formula III or IV ##STR6## wherein:
- R is alkyl, aryl, aralkyl, acyl or aroyl;
- X is oxygen or NH;
- when X is oxygen, R.sup.2 is alkyl, aryl, aralkyl, acyl or aroyl;
- when X is NH, R.sup.2 is acyl, aroyl, or alkylcarbamyl;
- and
- one of Z.sup.1 or Z.sup.2 is N.sub.3, and the other is H;
- comprising reacting a metal azide with a glycosyl phosphate triester having the phosphate group cis to the adjacent C-2 substituent at a temperature of from about 40 degrees Centigrade to about 80 degrees Centigrade wherein the glycosyl phosphate triester is a compound of Formula I or II ##STR7## wherein:
- R is alkyl, aryl, aralkyl, acyl or aroyl;
- X is oxygen or NH;
- when X is oxygen R.sup.2 is alkyl, aryl, aralkyl, acyl or aroyl, when X is NH, R.sup.2 is acyl, aroyl, or alkylcarbamyl;
- one of Y.sup.1 or Y.sup.2 is O--P.uparw.O(OR.sup.4).sub.2
- and the other is H;
- and
- R.sup.4 is aryl
- and wherein the reaction is carried out in the presence of a polar, aprotic solvent.
12 more elements
Dependencies are inferred from the claim text.