17495-10-2

Basic information

• Product Name: N²-acetyl-7-benzylguanine
• Synonyms: N²-acetyl-7-benzylguanine
• CAS NO: 17495-10-2
• Molecular Weight: 283.29
• Mol File: 17495-10-2.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: N²-acetyl-7-benzylguanine(CAS DataBase Reference)
• NIST Chemistry Reference: N²-acetyl-7-benzylguanine(17495-10-2)
• EPA Substance Registry System: N²-acetyl-7-benzylguanine(17495-10-2)

Safety Data

• Hazardous Substances Data: 17495-10-2(Hazardous Substances Data)

Upstream product

• 100-39-0 benzyl bromide 
• 73-40-5 2-amino-1,9-dihydro-6H-purin-6-one 
• 6979-94-8 2',3',5'-tri-O-acetyl-guanosine 
• 118-00-3 G 
• 100-44-7 benzyl chloride 
• 108-24-7 acetic anhydride 
• 17495-12-4 2-amino-7-benzyl-1H-purin-6(7H)-one 

Downstream Products

• 204515-22-0 2-acetyl-7-benzyl-9-[(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl)ethyl]guaninium inner salt 
• 81777-40-4 2-acetoxyethoxymethyl bromide 
• 33147-25-0 2-[2-(guanin-9-yl)ethyl]butanoic acid 
• 39809-25-1 Penciclovir 
• 97845-60-8 9-<4-acetoxy-3-(acetoxymethyl)butyl>-2-amino-6-chloro-9H-purine 
• 97845-72-2 2-[(acetyloxy)methyl]-4-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)butyl acetate 
• 17495-12-4 2-amino-7-benzyl-1H-purin-6(7H)-one 
• 17495-11-3 N²-acetyl-9-benzylguanine 
• 14937-72-5 9-benzylguanine 
• 104227-87-4 9-(4-acetoxy-3-acetoxymethylbutyl)-2-aminopurine 
• 127205-22-5 7-[4-hydroxy-3-(hydroxymethyl)but-1-yl]guanine 
• 104227-86-3 6-deoxypenciclovir 
• 794497-80-6 5-[2-(N²-acetyl-9-benzylguanin-7-yl)ethyl]-2,2-dimethyl-1,3-dioxacyclohexane-4,6-dione 
• 256945-24-1 7-(4-acetoxybut-1-yl)-2-acetylamino-6-(2',4',6'-triisopropylbenzenesulfonyloxy)-7H-purine 

Relevant articles and documents

Practical syntheses of penciclovir and famciclovir from N2-acetyl-7-benzylguanine

We have established practical methods for the synthesis of penciclovir (PCV) and famciclovir (FCV) from readily available guanosine via N2-acetyl-7-benzylguanine. The alkylation of N2-acetyl-7-benzylguanine proceeded selectively at the N9 position to give the desired alkylated product in good yield in salt form. After conventional catalytic hydrogenolysis of the benzyl group and hydrolysis of the resulting acetate, pure PCV was obtained without the need for chromatography. As a side chain precursor, the mesylate was selected rather than a halide since the corresponding halides gave several impurities under the same reaction conditions. Two procedures for the synthesis of FCV from PCV and a derivative are also reported.

Process for producing purine derivatives

A process for preparing 7-benzylpurine derivatives is provided. An acetylpurine nucleoside is reacted with a benzyl halide to benzylate the 7-position of the purine base, and an acid is then added to the reaction mixture to hydrolyze the glycoside bond. The 7-benzylpurines may be used to prepare 9-substituted purine derivatives.