Premium
Bis(2,2,2‐trichloro‐1,1‐dimethylethyl) Monochlorophosphate, a Selective Reagent for the Phosphorylation and Protection of the 5′‐OH Group of Nucleoside Derivatives
Author(s) -
Kellner Herbert A.,
Schneiderwind Ruth G. K.,
Eckert Heiner,
Ugi Ivar K.
Publication year - 1981
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.198105771
Subject(s) - reagent , protecting group , nucleoside , oligonucleotide , chemistry , residue (chemistry) , phosphorylation , cleavage (geology) , phosphate , thymidine , group (periodic table) , combinatorial chemistry , stereochemistry , biochemistry , organic chemistry , dna , biology , alkyl , paleontology , fracture (geology)
The selective protection of the 5′‐position of thymidine (2) can be accomplished with the reagent (1) , R = Cl 3 CC(CH 3 ) 2 . The protecting group survives all reactions necessary for oligonucleotide syntheses. The 5′‐phosphate (3) can then be obtained by reductive cleavage of residue R—without intermediary regeneration of a free 5′‐OH group.