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Stereoselective Synthesis of R P ‐ and S P ‐Dithymidine Phosphorothioates via Chiral Indolooxazaphosphorine Intermediates Derived from Tryptophan
Author(s) -
Lu Yixin,
Just George
Publication year - 2000
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/1521-3773(20001215)39:24<4521::aid-anie4521>3.0.co;2-m
Subject(s) - enantiomer , stereoselectivity , tryptophan , chemistry , oligonucleotide , stereochemistry , residue (chemistry) , combinatorial chemistry , organic chemistry , biochemistry , amino acid , catalysis , gene
A chiral auxiliary 1 and its enantiomer, which are easily prepared from L ‐ and D ‐tryptophan, facilitate diastereoselective syntheses of phosphorothioate oligonucleotides. Phosphorothioate 2 was obtained from 1 in five steps with over 95 % de , and the enantiomer of 1 afforded ( S P )‐ 2 with an equally good de value. T=thymine residue.