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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

1981; Wiley; Volume: 20; Issue: 6-7 Linguagem: Inglês

10.1002/anie.198105771

1521-3773

Herbert A. Kellner, Ruth G. K. Schneiderwind, Heiner Eckert, Ivar Ugi,

Chemical Synthesis and Analysis

The selective protection of the 5′-position of thymidine (2) can be accomplished with the reagent (1), R = Cl3CC(CH3)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.