Convenient synthesis of (E)-5-aminoallyl-2′-deoxycytidine and some related derivatives
MV Reddington, D Cunninghan-Bryant
Index: Reddington, Mark V.; Cunninghan-Bryant, Daniel Tetrahedron Letters, 2011 , vol. 52, # 2 p. 181 - 183
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Citation Number: 15
Abstract
Preparation via the Heck reaction of 5-(E)-(3-trifluoroacetamidoallyl)-2′-deoxycytidine (3a) and some N4-formamidine protected derivatives is reported. Difficulties with coupling N-allyl- trifluoroacetamide to 5-iodo-2′-deoxycytidine were overcome by using Pd2 (dba) 3 as catalyst and temporary dimethylformamidine protection of the N4-amine of the nucleoside. Compound 3a was isolated with 60% overall yield by crystallization.
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