Processes for high-yield diastereoselective synthesis of dideoxy

Details Processes for high-yield diastereoselective synthesis of dideoxy Processes for high-yield diastereoselective synthesis of dideoxy

1996-06-14

1999-12-21

Kight, John

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

Organic compounds

Carbohydrates or derivatives

536 2714, 536 282, C07H 1904

Patent

active

060050977

ABSTRACT:
The present invention relates to methods for substantially enhancing the stereoselective synthesis of .beta.-anomeric nucleoside analogs. In methods according to the present invention, the introduction of a phenylseleno group onto a blocked lactone sugar precursor may be selected so that the desirable phenylseleno substituent is introduced on the side of the blocked lactone away from the blocking group. This stereospecific introduction of the phenylseleno group in sugar precursor allows the synthesis of nucleoside analogs and in particular, 2',3',-dideoxy- and 2',3'-dideoxy-2',3'-didehydronucleoside analogs in very high yield. In certain preferred embodiments, the preferred phenylseleno blocked lactone is obtained in an amount representing approximately 90% or more of the total amount of the stereoisomers obtained. In even more preferred embodiments, the amount of the preferred stereoisomer is at least 95%, even more preferably at least about 97% of the total amount of phenylseleno blocked lactone produced.

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