High-yield regioselective synthesis of 9-glycosyl guanine nucleosides and analogues via coupling with 2-N-acetyl-6-O-diphenylcarbamoylguanine
- 1 June 1987
- journal article
- research article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 65 (6) , 1436-1437
- https://doi.org/10.1139/v87-243
Abstract
Treatment of 2-N,9-diacetylguanine with diphenylcarbamoyl chloride followed by heating with aqueous ethanol gave 2-N-acetyl-6-O-diphenylcarbamoylguanine (2-acetamido-6-diphenylcarbamoyloxypurine). Bis-trimethylsilylation of this product followed by coupling with glycosyl acetates (trimethylsilyl triflate catalysis) or α-haloethers in anhydroustoluene gave 9-substituted guanine compounds in high yields with no 7-isomers detected.This publication has 2 references indexed in Scilit:
- Nucleoside syntheses, XXII1)Nucleoside synthesis with trimethylsilyl triflate and perchlorate as catalystsEuropean Journal of Inorganic Chemistry, 1981
- Selectivity of action of an antiherpetic agent, 9-(2-hydroxyethoxymethyl)guanineProceedings of the National Academy of Sciences, 1977