Polymer-bound oxathiaphospholane: a solid-phase reagent for regioselective monothiophosphorylation and monophosphorylation of unprotected nucleosides and carbohydrates.
Two polymers bound to N,N-diisopropylamino-1,3,2-oxathiaphospholane were reacted with unprotected carbohydrates and nucleosides in the presence of 1H-tetrazole, followed by oxidation with tert-butyl hydroperoxide or sulfurization with Beaucage's reagent. The 1,3,2-oxathiaphospholane ring-opening with 3-hydroxypropionitrile, followed by treatment with DBU, afforded the corresponding monophosphate and monothiophosphate derivatives, respectively, through the elimination of polymer-bound ethylene episulfide. Reactions using this strategy offer the advantages of high regioselectivity, monosubstitution, and facile isolation and recovery of products.
Ahmadibeni
Yousef
Y
Department of Biomedical and Pharmaceutical Sciences, College of Pharmacy, The University of Rhode Island, Kingston, 02881, USA.
Parang
Keykavous
K
D002241:Carbohydrates / Q000737:chemistry*; D007202:Indicators and Reagents; D009705:Nucleosides / Q000737:chemistry*; D009711:Nucleotides / Q000737:chemistry*; D011108:Polymers / Q000737:chemistry*; D012266:Ribose / Q000031:analogs & derivatives* / Q000737:chemistry; D013237:Stereoisomerism
D002241:Carbohydrates; D007202:Indicators and Reagents; D009705:Nucleosides; D009711:Nucleotides; D011108:Polymers; C434797:oxathiaphospholane; D012266:Ribose