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 | Zendy

Kellner Herbert A. | Zendy; Schneiderwind Ruth G. K. | Zendy; Eckert Heiner | Zendy; Ugi Ivar K. | Zendy

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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.

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