Process for preparing 3-deoxy-B-D-threo-pentofuranosyl nucleosides
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United States of America Patent
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Dec 19, 1995
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N/A
app pub date -
Apr 2, 1992
filing date -
Apr 23, 1987
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Abstract
A process for preparing 3-deoxy-.beta.-D-threo-pentofuransyl nucleosides having the formula (II') shown below: ##STR1## wherein B is a purine, pyrimidine, a protected purine or a protected pyrimidine, and R.sup.4 is a hydroxyl protecting group; comprising treating a compound of formula (I'): ##STR2## wherein B is a purine, a protected purine, a pyrimidine or a protected pyrimidine; R.sup.1 is pivaloyl, tosyl, dimethoxytrityl, benzoyl, or hydroxyl; R.sup.2 is mesyl, triflate, or tosyl; and R.sup.3 is pivaloyl, tosyl, dimethoxytrityl, benzoyl, and hydroxyl with a base--an alkaki metal lower alkoxide, an alkaline earth metal lower alkoxide, sodium hydroxide, or potassium hydroxide--along with a reducing agent--an alkali metal borohydride, an alkaline earth metal borohydride, tetraalkylammonium borohydride in an alcohol solvent at a temperature of from 0.degree. C. to 100.degree. C. for five minutes to two hours. The resulting 3'-deoxy-.beta.-D-threo-pentofuranosyl nucleosides are antiviral.
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