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

Autor:	Takayoshi Torii, Hiroshi Shiragami, Keizo Yamashita, Yumiko Suzuki, Toyoto Hijiya, Tatsuki Kashiwagi, Kunisuke Izawa
Rok vydání:	2006
Předmět:	Mesylate Organic Chemistry Famciclovir Alkylation complex mixtures Biochemistry Combinatorial chemistry chemistry.chemical_compound chemistry Hydrogenolysis Yield (chemistry) Penciclovir Drug Discovery medicine Benzyl group Organic chemistry Derivative (chemistry) medicine.drug
Zdroj:	Tetrahedron. 62:5709-5716
ISSN:	0040-4020
DOI:	10.1016/j.tet.2006.03.080
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::fd35ac4c60c60dce9a9f1baf03ab741b https://doi.org/10.1016/j.tet.2006.03.080 Zobrazit plný text záznamu Full Text from ScienceDirect