title: Synthesis of N-homobicyclic dideoxynucleoside analogues.
abstract: Syntheses of six N-homobicyclic dideoxynucleoside analogues are described. The reaction of mannose diacetonide with trimethylsulfoxonium iodide gave a mixture of diastereomeric hydroxymethyl mannose diacetonides in a ratio of 2:5, which was separated by fractional crystallization. The two stereoisomers were converted to bicyclic furanolactols each of which was coupled with three nucleoside bases. Further debenzylations gave the six target N-homobicyclic dideoxynucleosides.
authors.affiliation: Organic Chemistry Division-I, Indian Institute of Chemical Technology, Hyderabad 500 007, India.
authors.forename: N
authors.initials: N
authors.lastname: Raghavendra Swamy
authors.forename: N
authors.initials: N
authors.lastname: Suryakiran
authors.forename: P
authors.initials: P
authors.lastname: Paradesi Naidu
authors.forename: Y
authors.initials: Y
authors.lastname: Venkateswarlu
mesh_terms: D001643:Bridged Bicyclo Compounds / Q000737:chemistry*; D060326:Chemistry Techniques, Synthetic / Q000379:methods*; D015224:Dideoxynucleosides / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D001643:Bridged Bicyclo Compounds; D015224:Dideoxynucleosides