Synthesis of beta-thymidine

Details Synthesis of beta-thymidine Synthesis of beta-thymidine

1988-03-01

1990-04-03

Brown, Johnnie R.

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

Organic compounds

Carbohydrates or derivatives

536 41, 536 184, C07H 100

Patent

active

049142330

ABSTRACT:
A process is provided in which a mixture of alpha- and beta-anomers is converted selectively to the desired beta-thymidine. The process involves the following steps: (a) converting a mixture of alpha- and beta-anomers of tetra-O-acylribofuranose to tri-O-acyl-.beta.-ribothymidine; (b) converting tri-O-acyl-.beta.-ribothymidine to .beta.-ribothymidine; (c) converting .beta.-ribothymidine to 2,2'-anhydro-.beta.-thymidine; (d) converting 2,2'-anhydro-.beta.-thymidine to 2'-halo-2'-deoxy-5-methyluridine; and (e) converting 2'-halo-2'-deoxy-5-methyluridine to beta-thymidine. The mixture of alpha- and beta-anomers of tetra-O-acylribofuranose may be produced by any suitable procedure such as by converting lower alkyl ribofuranoside to the tetra-O-acylribofuranose mixture. The lower alkyl ribofuranosides may in turn be produced by various methods. However, a desirable way of effecting this conversion involves use of D-ribose as the starting material which is converted to the lower alkyl ribofuranoside.

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