97845-61-9

Basic information

• Product Name: 1,3-Propanediol, 2-[2-(2-amino-6-chloro-7H-purin-7-yl)ethyl]-, diacetate (ester)
• CAS NO: 97845-61-9
• Molecular Formula: C14H18ClN5O4
• Mol File: 97845-61-9.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 1,3-Propanediol, 2-[2-(2-amino-6-chloro-7H-purin-7-yl)ethyl]-, diacetate (ester)(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Propanediol, 2-[2-(2-amino-6-chloro-7H-purin-7-yl)ethyl]-, diacetate (ester)(97845-61-9)
• EPA Substance Registry System: 1,3-Propanediol, 2-[2-(2-amino-6-chloro-7H-purin-7-yl)ethyl]-, diacetate (ester)(97845-61-9)

Safety Data

• Hazardous Substances Data: 97845-61-9(Hazardous Substances Data)

Upstream product

• 10310-21-1 2-Amino-6-chloropurin 
• 126589-82-0 2-Acetoxymethyl-4-bromobut-1-yl acetate 
• 131266-10-9 2-acetoxymethyl-4-benzyloxybutyl acetate 
• 128139-38-8 Acetic acid 2-acetoxymethyl-4-methanesulfonyloxy-butyl ester 
• 77661-80-4 2-(2-(benzyloxy)ethyl)propane-1,3-diol 
• 225111-63-7 diethyl <2-(1-ethoxyethoxy)ethyl>malonate 
• 225111-64-8 1-acetoxy-2-acetoxymethyl-4-(1-ethoxyethoxy)butane 
• 126589-88-6 1,3-diacetoxy-2-(2-hydroxyethyl)propane 
• 127047-77-2 4-acetoxy-3-(acetoxymethyl)-1-iodobutane 

Relevant articles and documents

Convenient syntheses of 9-[4-hydroxy-3-(hydroxymethyl)butyl]guanine (penciclovir) and 9-[4-acetoxy-3-(acetoxymethyl)butyl]-2-amino-9h-purine (famciclovir)

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 123 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% yield. Acidic hydrolysis of the latter compound 26 gave penciclovir 4 in virtually quantitative yield. Penciclovir 4 and famciclovir 5 were prepared from 2- amino-6-[(4-chlorophenyl)sulfanyl]purine 9a in four and five steps, respectively, by procedures involving initial alkylation with 1,2- dibromoethane. The overall yields obtained were 65 and ca. 60%, respectively.

Antiviral guanine derivatives

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