Open AccessStereoselective synthesis of dinucleoside phosphorothioate using enantiopure 1,2-amino alcohols as chiral auxiliaries
Author(s) -
Natsuhisa Oka,
Takeshi Wada,
Kazuhiko Saigo
Publication year - 2001
Publication title -
nucleic acids symposium series
Language(s) - English
Resource type - Journals
eISSN - 1746-8272
pISSN - 0261-3166
DOI - 10.1093/nass/1.1.13
Subject(s) - enantiopure drug , stereoselectivity , nucleoside , chemistry , activator (genetics) , yield (engineering) , condensation , organic chemistry , stereochemistry , combinatorial chemistry , catalysis , enantioselective synthesis , biochemistry , materials science , gene , thermodynamics , physics , metallurgy
Diastereopure nucleoside 3'-cyclic phosphoramidites were synthesized stereoselectively from enantiopure 1,2-amino alcohols. In the presence of a novel activator, these phosphoramidites underwent the condensation with 3'-O-tert-butyldimethylsilylthymidine to give the corresponding phosphite intermediates. Upon sulfurization, followed by deprotection, dithymidine phosphorothioate was obtained in good yield with good to excellent diastereoselectivity.
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