Method of manufacturing 2',3'-dideoxy-2',3'-didehydronucleosides

Details Method of manufacturing 2',3'-dideoxy-2',3'-didehydronucleosides Method of manufacturing 2',3'-dideoxy-2',3'-didehydronucleosides

1992-03-20

1993-11-23

Brown, Johnnie R.

Organic compounds -- part of the class 532-570 series

Organic compounds

Carbohydrates or derivatives

536 282, C07H 1900

Patent

active

052645614

ABSTRACT:
The instant invention is drawn to a method for manufacturing 2',3'-dideoxy-2',3'-didehydronucleoside compounds by reacting a ribonucleoside derivative wherein the hydroxyl in the 5'-position of the furanose ring of said ribonucleoside is protected by a silyl protective group, with an acid anhydride such as acetic anhydride in the presence of a catalyst such as hydrous zirconium oxide, and then subjecting the reaction product to decarboxylation. The decarboxylation can be effected by heating the reaction product. This method can be performed in a single step, and requires no reagents which are expensive or chemicals which should be handled with care. Hence, it serves to manufacture 2',3'-dideoxy-2',3'-didehydronucleosides easily at low cost.

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McCarthy et al. (1966) Jour. Am. Chem. Soc., 88(7) 1550-53.
Horwitz et al. (1967) Notes, vol. 32, pp. 817-818.
Griffin et al. (1967) Tetrahedron (23) :2301-13.

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