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Biomimetic Phosphonylation and Phosphorylation of Glycoses and Deoxynucleosides
Author(s) -
Tzokov Svetomir B.,
Bratovanova Emilia K.,
Petkov Dimiter D.,
Devedjiev Ivan T.
Publication year - 1994
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199423021
Subject(s) - chemistry , epichlorohydrin , alkyl , alcohol , derivative (finance) , propylene oxide , phosphoric acid , organic chemistry , phosphorylation , thymidine , aldehyde , medicinal chemistry , dna , biochemistry , catalysis , ethylene oxide , copolymer , financial economics , economics , polymer
In a one‐pot reaction with yields of over 80% , phosphonic or phosphoric acids 1 (R 1 , R 2 = H/OH and OH/OH, respectively) react with glucose or thymidine (dimethoxytrityl derivative) as the alcohol, and propylene oxide or epichlorohydrin 2 (X = CH 3 and CH 2 Cl, respectively) as the condensation agent to give the respective alkyl phosphonates and phosphates 4 . The biomimetic reaction proceeds presumably via intermediate 3 .