5-fluoro-1-(3-deoxy-3-fluoro-4,6-O-isopropylidene-β-D-glucopyranosyl-2-ulose)uracil | 870122-88-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: 5-fluoro-1-(3-deoxy-3-fluoro-4,6-O-isopropylidene-β-D-glucopyranosyl-2-ulose)uracil
• 英文别名: 1-[(4aR,6R,8S,8aR)-8-fluoro-2,2-dimethyl-7-oxo-4,4a,8,8a-tetrahydropyrano[3,2-d][1,3]dioxin-6-yl]-5-fluoropyrimidine-2,4-dione
• CAS: 870122-88-6
• 化学式: C₁₃H₁₄F₂N₂O₆
• 分子量: 332.261
• InChiKey: ZAGVPAAHUAPEJZ-LUQPRHOASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  94.2
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5-fluoro-1-(3-deoxy-3-fluoro-4,6-O-isopropylidene-β-D-glucopyranosyl-2-ulose)uracil 在 吡啶 、 IR 120 resin 作用下， 以 甲醇 为溶剂， 反应 6.0h， 生成 5-fluoro-1-(6-O-acetyl-3,4-dideoxy-3-fluoro-β-D-glycero-hex-3-enopyranosyl-2-ulose)uracil
  参考文献：
  名称：

  New Short Route to Unsaturated Fluoroketonucleosides: Case of 5-Fluoro-1-(6-O-Acetyl-3,4-Di-Deoxy-3-Fluoro-β-d-Glycero-Hex-3-Eno-Pyranos-2-Ulosyl) Uracil

  摘要：

  The proposed short synthesis involves two key steps: Oxidation of the isopropylidene derivative of the 3-fluoronucleoside possessing a free hydroxyl group in 2-position and acetylation of deprotected 3-fluoro-2-ketonucleoside which, after a beta-elimination reaction, gives the desired unsaturated ketonucleoside 5.

  DOI：

  10.1081/ncn-59683
• 作为产物：
  描述：

  5-fluoro-1-(3-deoxy-3-fluoro-4,6-O-isopropylidene-β-D-glucopyranosyl)uracil 在 重铬酸吡啶 、 3 A molecular sieve 、 溶剂黄146 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 5.0h， 以50%的产率得到5-fluoro-1-(3-deoxy-3-fluoro-4,6-O-isopropylidene-β-D-glucopyranosyl-2-ulose)uracil
  参考文献：
  名称：

  New Short Route to Unsaturated Fluoroketonucleosides: Case of 5-Fluoro-1-(6-O-Acetyl-3,4-Di-Deoxy-3-Fluoro-β-d-Glycero-Hex-3-Eno-Pyranos-2-Ulosyl) Uracil

  摘要：

  The proposed short synthesis involves two key steps: Oxidation of the isopropylidene derivative of the 3-fluoronucleoside possessing a free hydroxyl group in 2-position and acetylation of deprotected 3-fluoro-2-ketonucleoside which, after a beta-elimination reaction, gives the desired unsaturated ketonucleoside 5.

  DOI：

  10.1081/ncn-59683

文献信息

• New Short Route to Unsaturated Fluoroketonucleosides: Case of 5-Fluoro-1-(6-O-Acetyl-3,4-Di-Deoxy-3-Fluoro-β-<scp>d</scp>-<i>Glycero</i>-Hex-3-Eno-Pyranos-2-Ulosyl) Uracil
  作者：Marie-José Egron、Dimitri Komiotis、Ismet Dorange、Jean Herscovici、Abraham P. Ollapally、Kostas Antonakis

  DOI：10.1081/ncn-59683

  日期：2005.3

  The proposed short synthesis involves two key steps: Oxidation of the isopropylidene derivative of the 3-fluoronucleoside possessing a free hydroxyl group in 2-position and acetylation of deprotected 3-fluoro-2-ketonucleoside which, after a beta-elimination reaction, gives the desired unsaturated ketonucleoside 5.