Selective diphosphorylation, dithiodiphosphorylation, triphosphorylation, and trithiotriphosphorylation of unprotected carbohydrates and nucleosides

Yousef Ahmadibeni, Keykavous Parang

Research output: Contribution to journalArticle

Abstract

(Chemical Equation Presented) Aminomethyl polystyrene resin-bound linkers of p-acetoxybenzyl alcohol were subjected to reactions with diphosphitylating and triphosphitylating reagents to yield the corresponding polymer-bound diphosphitylating and triphosphitylating reagents, respectively. A number of unprotected carbohydrates and nucleosides were reacted with the polymer-bound reagents. Oxidation with tert-butyl hydroperoxide or sulfurization with Beaucage's reagent, followed by removal of cyanoethoxy group with DBU and the acidic cleavage, respectively, afforded only one type of monosubstituted nucleoside and carbohydrate diphosphates, dithiodiphosphates, triphosphates, and trithiotriphosphates with high regioselectivity.

Original languageEnglish (US)
Pages (from-to)5589-5592
Number of pages4
JournalOrganic Letters
Volume7
Issue number25
DOIs
StatePublished - Dec 8 2005
Externally publishedYes

ASJC Scopus subject areas

  • Molecular Medicine

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