Convenient syntheses of 9-[4-hydroxy-3-(hydroxymethyl) butyl] guanine (penciclovir) and 9-[4-acetoxy-3-(acetoxymethyl) butyl]-2-amino-9H-purine (famciclovir)
B Brand, CB Reese, Q Song, C Visintin
Index: Brand, Briony; Reese, Colin B.; Song, Quanlai; Visintin, Cristina Tetrahedron, 1999 , vol. 55, # 16 p. 5239 - 5252
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Citation Number: 26
Abstract
Guanine 11 was converted, in a one pot reaction, into 2-amino-6-[(4-chlorophenyl) sulfanyl] purine 9a in 88% isolated yield. 4-Acetoxy-3-(acetoxymethyl) butanol 23 was prepared from 2-chloroethanol in five steps and in 46% overall yield. The mesylate ester of compound 23 reacted with 9a in the presence of potassium carbonate with a high degree of regioselectivity (89%) to give the N− 9 alkylated product 26 which was isolated in 80% ...
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