(formula presented) A conformationally locked carbocyclic version of puromycin amino nucleoside was synthesized via Mitsunobu coupling of a 3-azido-substituted carbocyclic moiety with 6-chloropurine without interference from the azido group reacting with triphenylphosphine. The requisite 3-azido-substituted carbocyclic pseudosugar was prepared by a double inversion of configuration at C3′ (nucleoside numbering) involving a nucleophilic displacement with azide.
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry