TY - JOUR
T1 - Solid-phase synthesis of symmetrical 5′,5′-dinucleoside mono-, di-, tri-, and tetraphosphodiesters
AU - Ahmadibeni, Yousef
AU - Parang, Keykavous
PY - 2007/10/25
Y1 - 2007/10/25
N2 - (Chemical Equation Presented) Four classes of phosphitylating reagents were subjected to reactions with aminomethyl polystyrene resin-bound p-acetoxybenzyl alcohol to yield the corresponding polymer-bound mono-, di-, tri-, and tetraphosphitylating reagents. The solid-phase reagents were reacted with unprotected nucleosides (e.g., thymidine, adenosine, 3′-azido-3′- deoxythymidine, cytidine, or inosine) in the presence of 5-(ethylthio)-1H- tetrazole. Polymer-bound nucleosides underwent oxidation with fert-butyl hydroperoxide, deprotection of cyanoethoxy groups with DBU, and the acidic cleavage, respectively, to afford 5′,5′-dinucleoside mono-, di-, tri-, and tetraphosphodiesters in 59-78% yield.
AB - (Chemical Equation Presented) Four classes of phosphitylating reagents were subjected to reactions with aminomethyl polystyrene resin-bound p-acetoxybenzyl alcohol to yield the corresponding polymer-bound mono-, di-, tri-, and tetraphosphitylating reagents. The solid-phase reagents were reacted with unprotected nucleosides (e.g., thymidine, adenosine, 3′-azido-3′- deoxythymidine, cytidine, or inosine) in the presence of 5-(ethylthio)-1H- tetrazole. Polymer-bound nucleosides underwent oxidation with fert-butyl hydroperoxide, deprotection of cyanoethoxy groups with DBU, and the acidic cleavage, respectively, to afford 5′,5′-dinucleoside mono-, di-, tri-, and tetraphosphodiesters in 59-78% yield.
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U2 - 10.1021/ol7018778
DO - 10.1021/ol7018778
M3 - Article
C2 - 17915884
AN - SCOPUS:35948985869
SN - 1523-7060
VL - 9
SP - 4483
EP - 4486
JO - Organic Letters
JF - Organic Letters
IS - 22
ER -