Stereoselective synthesis and X-ray structure of 1-(4-O-benzyl-1,5-anhydro-2,3-dideoxy-D-arabino-hex-1-enitol-3-yl )-4-me thoxy-1H-pyrimidin-2-one.
The intramolecular glycosylation of a 6-O-(4-methoxypyrimidin-2-yl) derivative of phenyl 2,3-didehydrohex-2-eno-1-thiopyranoside afforded 3-deoxy-3-(4-methoxypyrimidin-2-on-1-yl)glycal as the major product in a stereoselective manner. The isolated 3'-deoxyglycal nucleoside was characterized by X-ray and NMR spectral analyses.
Sugimura
H
H
Faculty of Education and Human Science, Yokohama National University, Japan. sugimura@edhs.ynu.ac.jp
D018360:Crystallography, X-Ray; D006031:Glycosylation; D009682:Magnetic Resonance Spectroscopy; D011741:Pyrimidine Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
C412237:1-(4-O-benzyl-1,5-anhydro-2,3-dideoxy-arabino-hex-1-enitol-3-yl)-4-methoxy-1H-pyrimidin-2-one; D011741:Pyrimidine Nucleosides