Purine acyclic nucleosides. Unambiguous synthesis of acyclovir  via  a furazano[3,4‐ d ]pyrimidine | Zendy

Kelley James L. | Zendy; Schaeffer Howard J. | Zendy

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Purine acyclic nucleosides. Unambiguous synthesis of acyclovir via a furazano[3,4‐ d ]pyrimidine

Author(s) -

Kelley James L.,

Schaeffer Howard J.

Publication year - 1986

Publication title -

journal of heterocyclic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.321

H-Index - 59

eISSN - 1943-5193

pISSN - 0022-152X

DOI - 10.1002/jhet.5570230156

Subject(s) - chemistry , pyrimidine , purine , alkylation , guanine , reductive amination , hydrolysis , ring (chemistry) , amination , cleavage (geology) , stereochemistry , ammonia , uracil , alkoxy group , medicinal chemistry , organic chemistry , nucleotide , dna , catalysis , biochemistry , alkyl , geotechnical engineering , fracture (geology) , engineering , gene , enzyme

Acyclovir was synthesized in five steps from 7‐formamido‐5‐methylthiofurazano[3,4‐ d ]pyrimidine 2 . Alkylation of 2 with 2‐(benzoyloxy)ethoxymethyl chloride, followed by reductive cleavage of the furazan ring gave 9‐[[2‐(benzoyloxy)ethoxy]methyl]‐2‐(methylthio)adenine 5 . Hydrolysis of the 6‐amino group of 5 , followed by amination of 7 with ammonia gave 9‐[(2‐hydroxyethoxy)methyl]guanine ( 1 , acyclovir).

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