title: Stereoselective cyclopropanation in the synthesis of 3'-deoxy-3'-C-hydroxymethyl-2',3'-methylene-uridine.
abstract: The synthesis of the novel 2',3'-cyclopropane nucleoside 3'-deoxy-3'-C-hydroxymethyl-2',3'-methylene-uridine is described. Stereoselective construction of the cyclopropane ring was achieved via Simmons-Smith cyclopropanation of a benzyl protected silyl enol ether, which was itself derived from 1,2-O-isopropylidene-α-D-xylofuranose.
authors.affiliation: Idenix Pharmaceuticals, 320 Bent Street, Cambridge, Massachusetts 02141, United States.
authors.forename: Zofia
authors.initials: Z
authors.lastname: Komsta
authors.forename: Benjamin A
authors.initials: BA
authors.lastname: Mayes
authors.forename: Adel
authors.initials: A
authors.lastname: Moussa
authors.forename: Montserrat
authors.initials: M
authors.lastname: Shelbourne
authors.forename: Alistair
authors.initials: A
authors.lastname: Stewart
authors.forename: Andrew J
authors.initials: AJ
authors.lastname: Tyrrell
authors.forename: Laura L
authors.initials: LL
authors.lastname: Wallis
authors.forename: Alexander C
authors.initials: AC
authors.lastname: Weymouth-Wilson
authors.forename: Alexander
authors.initials: A
authors.lastname: Yurek-George
mesh_terms: D003521:Cyclopropanes / Q000737:chemistry*; D015394:Molecular Structure; D009005:Monosaccharides / Q000737:chemistry; D013237:Stereoisomerism; D014529:Uridine / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology
chemical_list: C516586:1,2-isopropylidene-alpha-D-xylofuranose; C000599334:3'-deoxy-3'-C-hydroxymethyl-2',3'-methylene-uridine; D003521:Cyclopropanes; D009005:Monosaccharides; C030797:cyclopropane; D014529:Uridine