TY - JOUR
T1 - Application of a solid-phase β-triphosphitylating reagent in the synthesis of nucleoside β-triphosphates
AU - Ahmadibeni, Yousef
AU - Parang, Keykavous
PY - 2006/7/21
Y1 - 2006/7/21
N2 - A β-triphosphitylating reagent was subjected to reaction with aminomethyl polystyrene resin-bound p-acetoxybenzyl alcohol to yield the corresponding polymer-bound β-triphosphitylating reagent. The solid-phase reagent was reacted with unprotected nucleosides (e.g., 3′-azido-3′- deoxythymidine, cytidine, thymidine, uridine, inosine, or adenosine) in the presence of 1H-tetrazole. Polymer-bound nucleosides underwent oxidation with t-butyl hydroperoxide, deprotection of cyanoethoxy groups with DBU, and the acidic cleavage, respectively, to afford only monosubstituted 5′-O-β-triphosphorylated nucleosides.
AB - A β-triphosphitylating reagent was subjected to reaction with aminomethyl polystyrene resin-bound p-acetoxybenzyl alcohol to yield the corresponding polymer-bound β-triphosphitylating reagent. The solid-phase reagent was reacted with unprotected nucleosides (e.g., 3′-azido-3′- deoxythymidine, cytidine, thymidine, uridine, inosine, or adenosine) in the presence of 1H-tetrazole. Polymer-bound nucleosides underwent oxidation with t-butyl hydroperoxide, deprotection of cyanoethoxy groups with DBU, and the acidic cleavage, respectively, to afford only monosubstituted 5′-O-β-triphosphorylated nucleosides.
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U2 - 10.1021/jo0610107
DO - 10.1021/jo0610107
M3 - Article
C2 - 16839180
AN - SCOPUS:33746373528
SN - 0022-3263
VL - 71
SP - 5837
EP - 5839
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 15
ER -