A Convenient Synthesis of 9-(2-Hydroxyethoxymethyl)guanine (Acyclovir) and Related Compounds

• Published in: Chemical & pharmaceutical bulletin Vol. 36; no. 3; pp. 1153 - 1157
• Main Authors: YAMADA, KEIKO, MORI, TAKEO, MATSUMOTO, HIROATSU, TAKEUCHI, TADAO, MIZUNO, YOSHIHISA, KANEKO, CHISATO
• Format: Journal Article
• Language: English
• Published: TOKYO The Pharmaceutical Society of Japan 1988; 公益社団法人日本薬学会; Pharmaceutical Soc Japan; Maruzen; Japan Science and Technology Agency
• Subjects: acyclovir; Acyclovir - analogs & derivatives; Acyclovir - chemical synthesis; alkylation; antiherpetic agnet; Catalysis; Chemical Phenomena; Chemistry; Chemistry, Medicinal; Chemistry, Multidisciplinary; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings; Life Sciences & Biomedicine; N^2-acetylacyclovir; O-acetylacyclovir; Organic chemistry; p-toluenesulfonic acid; Pharmacology & Pharmacy; Physical Sciences; Preparations and properties; Science & Technology; Temperature; Acyclic nucleoside; Temperature; Nitrogen heterocycle; Deprotection; Herpes; Guanidines; Selectivity; Acid catalysis; Infection; Hydroxyether; Viral disease; Bicyclic compound; Antiviral
• ISSN: 0009-2363; 1347-5223
• DOI: 10.1248/cpb.36.1153

A convenient and economical synthesis of 9-(2-hydroxyethoxymethyl)guanine (1, acyclovir, Zovirax, or acyclic guanosine : an antiherpetic agent)from guanine was developed via N2, O-diacetylacyclovir. Two closely related compounds, N2-acetylacyclovir (7) and O-acetylacyclovir (8), were also prepared by selective deacetylation.