1-(5-deoxy-3-O-methyl-β-D-threo-pent-4-enofuranosyl)uracil | 250727-34-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1-(5-deoxy-3-O-methyl-β-D-threo-pent-4-enofuranosyl)uracil
• 英文别名: 1-[(2R,3S,4S)-3-hydroxy-4-methoxy-5-methylideneoxolan-2-yl]pyrimidine-2,4-dione
• CAS: 250727-34-5
• 化学式: C₁₀H₁₂N₂O₅
• 分子量: 240.216
• InChiKey: WDYPYBXKKRTDGA-DJLDLDEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  88.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(5-deoxy-3-O-methyl-β-D-threo-pent-4-enofuranosyl)uracil 在 硼烷四氢呋喃络合物 、 sodium hydroxide 、 双氧水 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 23.0h， 以53%的产率得到1-(3-O-methyl-α-L-xylo-furanosyl)uracil
  参考文献：
  名称：

  3′-Selective modification of a 4′,5′-didehydro-5′-deoxy-2′,3′-epoxyuridine using nucleophiles

  摘要：

  1-(2,3-Anhydro-5-deoxy-4,5-didehydro-alpha-(L)-erythro-pent-4-enofuranosyl)uracil 4 was obtained by the treatment of 5 '-iodo-2 ',3 '-epoxyuridine 5 with LiHMDS in excellent yield. The pyrimidine nucleoside 4 possesses quite unique vinyl epoxide moiety within the molecules. The reactions of 4 with a variety of nucleophiles gave 3 '-substituted pyrimidine nucleosides without the formation of the corresponding 2 '-substituted isomers. In the case of NaN3 or PhSH, the corresponding 5 '-adduct was obtained as a minor product together with the expected 3 '-adduct. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.06.053
• 作为产物：
  描述：

  1-(2,3-anhydro-5-deoxy-5-iodo-β-D-lyxofuranosyl)uracil 在 lithium hexamethyldisilazane 作用下， 以 甲醇 为溶剂， 反应 6.0h， 生成 1-(5-deoxy-3-O-methyl-β-D-threo-pent-4-enofuranosyl)uracil
  参考文献：
  名称：

  Formation of 4’,5’-Didehydro-5’-deoxy-3’-O-methyluridine via Regioselective Nucleophilic Addition of Methoxide Anion to 2’,3’-Anhydro-5’-dehydro-5’-iodouridine

  摘要：

  Treatment of 2',3'-anhydro-5'-deoxy-5'-iodouracil (1) with sodium methoxide regioselectively provided 4',5'-didehydro-5'-deoxy-3'-O-methyl-uridine (2) as the sole product via 4',5'-didehydro-5'-deoxy-2',3'-epoxyuridine (6) as an intermediate.

  DOI：

  10.3987/com-05-s(t)14

文献信息

• 3′-Selective modification of a 4′,5′-didehydro-5′-deoxy-2′,3′-epoxyuridine using nucleophiles
  作者：Hideki Takasu、Yoshie Tsuji、Hironao Sajiki、Kosaku Hirota

  DOI：10.1016/j.tet.2005.06.053

  日期：2005.8

  1-(2,3-Anhydro-5-deoxy-4,5-didehydro-alpha-(L)-erythro-pent-4-enofuranosyl)uracil 4 was obtained by the treatment of 5 '-iodo-2 ',3 '-epoxyuridine 5 with LiHMDS in excellent yield. The pyrimidine nucleoside 4 possesses quite unique vinyl epoxide moiety within the molecules. The reactions of 4 with a variety of nucleophiles gave 3 '-substituted pyrimidine nucleosides without the formation of the corresponding 2 '-substituted isomers. In the case of NaN3 or PhSH, the corresponding 5 '-adduct was obtained as a minor product together with the expected 3 '-adduct. (c) 2005 Elsevier Ltd. All rights reserved.
• Formation of 4’,5’-Didehydro-5’-deoxy-3’-O-methyluridine via Regioselective Nucleophilic Addition of Methoxide Anion to 2’,3’-Anhydro-5’-dehydro-5’-iodouridine
  作者：Hironao Sajiki、Hideki Takasu、Kosaku Hirota

  DOI：10.3987/com-05-s(t)14

  日期：——

  Treatment of 2',3'-anhydro-5'-deoxy-5'-iodouracil (1) with sodium methoxide regioselectively provided 4',5'-didehydro-5'-deoxy-3'-O-methyl-uridine (2) as the sole product via 4',5'-didehydro-5'-deoxy-2',3'-epoxyuridine (6) as an intermediate.