Stereoselective Synthesis and Conformational Study of Novel 2′,3′-Didehydro-2′,3′-dideoxy-4′-selenonucleosides

• Published in: Journal of organic chemistry Vol. 73; no. 11; pp. 4259 - 4262
• Main Authors: Tosh, Dilip K, Choi, Won Jun, Kim, Hea Ok, Lee, Yoonji, Pal, Shantanu, Hou, Xiyan, Choi, Jungwon, Choi, Sun, Jeong, Lak Shin
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 06.06.2008; Amer Chemical Soc
• Subjects: Carbohydrates. Nucleosides and nucleotides; Chemistry; Chemistry, Organic; Crystallography, X-Ray; Dideoxynucleosides - chemistry; Exact sciences and technology; Heterocyclic compounds; Magnetic Resonance Spectroscopy; Miscellaneous; Nucleic Acid Conformation; Nucleosides, nucleotides and oligonucleotides; Organic chemistry; Physical Sciences; Preparations and properties; Science & Technology; Selenium - chemistry; Spectrometry, Mass, Fast Atom Bombardment; Stereoisomerism; POTENT; 3'-AZIDO-3'-DEOXYTHYMIDINE; 1ST SYNTHESIS; 5'-TRIPHOSPHATE; ANALOGS; REVERSE-TRANSCRIPTASE; RESISTANCE; HUMAN-IMMUNODEFICIENCY-VIRUS; STAVUDINE; ANTI-HIV DRUGS; Organic selenide; Condensation reaction; Aldose; Nitrogen heterocycle; Pummerer reaction; Selenium heterocycle; Conformational analysis; Lactone; Oxygen heterocycle; X ray diffraction; Stereoselectivity; Organic thiocarbonate; Cyclic compound; Ribose; Molecular model; Force field method; Pyrimidine derivatives; Nucleoside; Chemical synthesis; Ethylenic compound
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo8003277

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 γ-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.