Synthesis and Structure Elucidation of (R)‐3‐(2′‐hydroxyprop‐1‐yl) adenine

Abstract

in Wiley Online Library (wileyonlinelibrary.com).(R)-3-(2′-hydroxyprop-1-yl) adenine 4 was obtained by alkylation of adenine 1 with R-propylene carbonate 2 in the presence of pulverized sodium hydroxide in the synthetic process of tenofovir. The elucidation of the structure of 4 was confirmed by single crystal X-ray diffraction and NMR experiments such as 1D 1 H, 13 C, and DEPT, as well as 2D COSY, HSQC, and HMBC spectra.

Solvent‐directed Regioselective Benzylation of Adenine: Characterization of N9‐benzyladenine and N3‐benzyladenine

“…The ratio of N9‐benzyladenine : N3‐benzyladenine can be varied to favor either product through the use of solvent, with N9‐benzyladenine favored in polar aprotic solvents and N3‐benzyladenine favored in polar protic solvents. Our work agrees well with the recently (2015) published work by Gao et al , who determined that the alkylation of adenine with R‐propylenecarbonate in the presence of pulverized sodium hydroxide in addition to the N9 regioisomer yields the N3‐subsitutent, (R)‐3‐(2′‐hydroxyprop‐1‐yl) adenine, not the N7‐regioisomer as reported by Raić et al Thus, surely the preference for N3 is probably general for all alkylation reactions, not just the benzylation.…”