Journal of Organic Chemistry 2005-02-04

Solid-phase reagents for selective monophosphorylation of carbohydrates and nucleosides.

Yousef Ahmadibeni, Keykavous Parang

文献索引：J. Org. Chem. 70(3) , 1100-3, (2005)

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摘要

Two classes of aminomethyl polystyrene resin-bound linkers of p-acetoxybenzyl alcohol were subjected to reactions with 2-cyanoethyl N,N-diisopropylchlorophosphoramidite to produce the corresponding polymer-bound phosphitylating reagents. These were reacted with a number of unprotected nucleosides and carbohydrates in the presence of 1H-tetrazole. Oxidation with tert-butyl hydroperoxide followed by removal of the cyanoethoxy group with 1,8-diazabicyclo[5.4.0]undec-7-ene afforded the corresponding polymer-bound phosphate diesters. Acidic cleavage of the p-acetoxybenzyl alcohol linker yielded monophosphorylated products with high regioselectivity and trapped linkers on the resins that can be reused.

相关化合物

  • 2-氰乙基 N,N-二异...

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