Stereoselective synthesis and conformational study of novel 2',3'-Didehydro-2',3'-dideoxy-4'-selenonucleosides.
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.
Tosh
Dilip K
DK
Laboratory of Medicinal Chemistry, College of Pharmacy, Ewha Womans University, Seoul, Korea.
Choi
Won Jun
WJ
Kim
Hea Ok
HO
Lee
Yoonji
Y
Pal
Shantanu
S
Hou
Xiyan
X
Choi
Jungwon
J
Choi
Sun
S
Jeong
Lak Shin
LS
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
D015224:Dideoxynucleosides; D012643:Selenium