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Study on the diastereoselective synthesis of dithymidine phosphorothioates through a d-xylose derived chiral auxiliary and development of a novel catalyst

✍ Scribed by Yixin Lu; George Just

Publisher: Elsevier Science
Year: 2000
Tongue: French
Weight: 64 KB
Volume: 41
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)01678-6

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✦ Synopsis

1,2-Di-O-isopropylidene-3-C-cyanoethyl-5-deoxy-5-isopropylamino-D-xylofuranose 16a was synthesized. The use of 16a as a chiral auxiliary led to the diastereoselective formation of dithymidine phosphorothioate. The chiral auxiliary was easily removed by treatment with concentrated ammonia. 2-Mesityl-4,5-dicyanoimidazole displays higher diastereoselectivity than the 2-bromo-4,5-dicyanoimidazole in the coupling reaction.

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