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Oxazaphosphorinane precursors to the diastereoselective synthesis of DNA phosphorothioates

โœ Scribed by Eric Marsault; George Just

Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
885 KB
Volume
53
Category
Article
ISSN
0040-4020

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โœฆ Synopsis

New chiral oxazaphosphorinanes were synthesized as potential precursors to chiral phosphite triesters.

Oxazaphosphorinanes 10 and 14 derived from cholesterol and camphor respectively were obtained as stable compounds. They led to rearrangement products in the acidic conditions required for coupling. Then, oxazaphosphorinane 22 derived from D-xylose was synthesized, and led to the diastereoselective synthesis of a T-T phosphorothioate dimer in a 28.5:1 (Rp)/(Sp) ratio.

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