Solid-phase reagents for selective monophosphorylation of carbohydrates and nucleosides

Yousef Ahmadibeni; Keykavous Parang

doi:10.1021/jo048113e

Solid-phase reagents for selective monophosphorylation of carbohydrates and nucleosides

Yousef Ahmadibeni, Keykavous Parang

Research output: Contribution to journal › Article › peer-review

22 Scopus citations

Abstract

(Chemical Equation Presented) 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 polymerbound 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.

Original language	English (US)
Pages (from-to)	1100-1103
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	70
Issue number	3
DOIs	https://doi.org/10.1021/jo048113e
State	Published - Feb 4 2005
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

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title = "Solid-phase reagents for selective monophosphorylation of carbohydrates and nucleosides",

abstract = "(Chemical Equation Presented) 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 polymerbound 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.",

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AU - Ahmadibeni, Yousef

AU - Parang, Keykavous

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N2 - (Chemical Equation Presented) 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 polymerbound 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.

AB - (Chemical Equation Presented) 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 polymerbound 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.

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Solid-phase reagents for selective monophosphorylation of carbohydrates and nucleosides

Abstract

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