title: A Claisen approach to 4'-Ed4T.
abstract: An efficient, stereoselective synthesis of 4'-Ed4T is demonstrated. The synthesis is highlighted by a regioselective TMSOTf-mediated acetal opening, a Claisen rearrangement to set the key 4'-stereocenter as well as the olefin, and a one-pot nonaflation/elimination to deliver the alkyne moiety. The synthesis proceeds in eight steps from 5-methyluridine and occurs in 37% overall yield.
authors.affiliation: Chemical Development, Bristol-Myers Squibb , 1 Squibb Drive, New Brunswick, New Jersey 08903, United States.
authors.forename: William P
authors.initials: WP
authors.lastname: Gallagher
authors.forename: Prashant P
authors.initials: PP
authors.lastname: Deshpande
authors.forename: Jun
authors.initials: J
authors.lastname: Li
authors.forename: Kishta
authors.initials: K
authors.lastname: Katipally
authors.forename: Justin
authors.initials: J
authors.lastname: Sausker
mesh_terms: D000475:Alkenes / Q000737:chemistry; D000480:Alkynes / Q000737:chemistry; D015394:Molecular Structure; D018119:Stavudine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism; D014529:Uridine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: C505960:4'-ethynylstavudine; D000475:Alkenes; D000480:Alkynes; C009182:ribothymidine; D018119:Stavudine; D014529:Uridine