Nucleic acid related compounds. 37. Convenient and high-yield syntheses of N-[(2-hydroxyethoxy)methyl] heterocycles as "acyclic nucleoside" analogues
- 1 March 1982
- journal article
- research article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 60 (5) , 547-553
- https://doi.org/10.1139/v82-081
Abstract
Treatment of 1,3-dioxolane with acetyl bromide gave (2-acetoxyethoxy)methyl bromide (2a) in an 88% yield. Several pyrimidines and 3 chloropurines were trimethylsilylated and coupled with 2a. The respective N-1 and N-9 alkylated products (obtained in 79-89% yields) were deacetylated to give N-[(2-hydroxyethoxy)methyl] heterocycles. The 6-amino or 6-chloro substituent of the 2-amino-6-substituted-purine derivatives was hydrolyzed smoothly with adenosine deaminase to give 9-[(2-hydroxyethoxy)methyl]guanine (acycloguanosine), the potent antiviral agent.Keywords
This publication has 1 reference indexed in Scilit:
- Selectivity of action of an antiherpetic agent, 9-(2-hydroxyethoxymethyl)guanineProceedings of the National Academy of Sciences, 1977