title: Stereoselective synthesis and conformational study of novel 2',3'-Didehydro-2',3'-dideoxy-4'-selenonucleosides.
abstract: Stereoselective synthesis of novel 2',3'-didehydro-2',3'-dideoxy-4'-selenonucleosides (4'-seleno-d4Ns) 4a- c was accomplished via 4'-selenoribofuranosyl pyrimidines 11a- c, as key intermediates. 4'-Selenoribofuranosyl pyrimidines 11a- c were efficiently synthesized from d-ribose or d-gulonic gamma-lactone using a Pummerer-type condensation as a key step. Introduction of 2',3'-double bond was achieved by treating cyclic 2',3'-thiocarbonate with 1,3-dimethyl-2-phenyl-1,3,2-diazaphospholidine.
authors.affiliation: Laboratory of Medicinal Chemistry, College of Pharmacy, Ewha Womans University, Seoul, Korea.
authors.forename: Dilip K
authors.initials: DK
authors.lastname: Tosh
authors.forename: Won Jun
authors.initials: WJ
authors.lastname: Choi
authors.forename: Hea Ok
authors.initials: HO
authors.lastname: Kim
authors.forename: Yoonji
authors.initials: Y
authors.lastname: Lee
authors.forename: Shantanu
authors.initials: S
authors.lastname: Pal
authors.forename: Xiyan
authors.initials: X
authors.lastname: Hou
authors.forename: Jungwon
authors.initials: J
authors.lastname: Choi
authors.forename: Sun
authors.initials: S
authors.lastname: Choi
authors.forename: Lak Shin
authors.initials: LS
authors.lastname: Jeong
mesh_terms: D018360:Crystallography, X-Ray; D015224:Dideoxynucleosides / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D009690:Nucleic Acid Conformation; D012643:Selenium / Q000737:chemistry*; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013237:Stereoisomerism
chemical_list: D015224:Dideoxynucleosides; D012643:Selenium