Tetrahedron

Alkylation of adenine with functionalized tert.-Propargyl carbonates. Synthesis of 3′-hydroxymethyladenallene—A new analogue of 2′-deoxyadenosine

ZQ Xu, RV Joshi, J Zemlicka

Index: Xu, Ze-Qi; Joshi, Ramachandra V.; Zemlicka, Jiri Tetrahedron, 1995 , vol. 51, # 1 p. 67 - 76

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Citation Number: 18

Abstract

Esters 9d–9g derived from acetylenic carbinol 5 were prepared and they were studied as potential alkylating agents with adenine (10), N6-benzoyl-and N6-dimethylamino- methyleneadenine (16 and 17). Carbonates 9f and 9g were the most suitable giving allene 11 and acetylene 12 (after N-deprotection in case of 16 and 17). On a scale larger than 0.2 mmol, slow addition of carbonate 9f or 9g to a solution of 10, 16 or 17 in DMF at 60° C was ...