Katagiri N, Haneda T, Kaneko C
Nucleic Acids Symp Ser. 1985(16):113-6.
The photochemical reaction of 3-deazauridines was investigated with the intention of obtaining chiral beta-lactams. Irradiation of appropriately protected 3-deazauridines at greater than or equal to 300 nm gave 2-(protected D-ribofuranosyl)-3-oxo-2-azabicyclo[2.2.0]hex-5-enes as a mixture of diasteromers, which were chromatographically separable. Treatment of each isomer with acid, such as trifluoroacetic acid, afforded the 5-oxo derivatives which by methanolysis gave rise to the corresponding chiral 4-methoxy-carbonylmethyl-1-(protected D-ribofuranosyl)azetidin-2-ones in good yields.
为了获得手性β-内酰胺，对3-脱氮尿苷的光化学反应进行了研究。在大于或等于300nm的波长下照射适当保护的3-脱氮尿苷，得到2-(保护的D-呋喃核糖基)-3-氧代-2-氮杂双环[2.2.0]己-5-烯，为非对映异构体混合物，可通过色谱法分离。用酸（如三氟乙酸）处理每种异构体，得到5-氧代衍生物，该衍生物经甲醇解后以良好的产率得到相应的手性4-甲氧基羰基甲基-1-(保护的D-呋喃核糖基)氮杂环丁烷-2-酮。
