Process for preparing 2',3'-Dideoxy-2',3'-dehydronucleosides

Details Process for preparing 2',3'-Dideoxy-2',3'-dehydronucleosides Process for preparing 2',3'-Dideoxy-2',3'-dehydronucleosides

1994-08-25

1997-04-29

Kunz, Gary L.

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

Organic compounds

Carbohydrates or derivatives

536 282, C07H 100, C07H 19073

Patent

active

056250576

ABSTRACT:
A process for preparing a 2', 3'-dideoxy-2',3'-didehydropyrimidine nucleoside comprising reacting the pyrimidine ribofuranoside with a trialkyl orthoester to yield the 2',3'-O-alkoxyethylidene derivative; which is reacted with hydrogen bromide in acetic acid or acetyl bromide to yield the 2-deoxy-2'-bromo-3'-acetyl-pyrimidine nucleoside; which is then reduced with zinc to yield the 2',3'-olefin of the pyrimidine nucleoside.

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patent: 5336770 (1994-08-01), Shiragami et al.
Patent Abstracts of Japan, vol. 13, No. 72 (C-570)(3420), Feb. 17, 1989, & JP-63-264-596, Nov. 1, 1988, Hiroshi Shiragami, et al., "Production of Didehydronucleosides".
Patent Abstracts of Japan, vol. 9, No. 166 (C-290)(1889), Jul. 11, 1985 & JP-60-38-395, Feb. 27, 1985, Takao Takahara, et al., "Preparation of 5-Fluorocytidine".
The Journal of Organic Chemistry, vol. 54, pp. 4780-4785, 1989, M. M. Mansuri, et al., "Preparation of 1-(2,3-Dideoxy-.beta.-D-Glycero-Pent-2-Enofuranosyl) Thymine (d4T).sup.1 and 2',3'-Dideoxyadenosine (dda) . . . ".

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