Acetic acid (2S,3S,4S,5R)-2-acetoxy-5-acetoxymethyl-4-iodo-tetrahydro-furan-3-yl ester | 74580-84-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid (2S,3S,4S,5R)-2-acetoxy-5-acetoxymethyl-4-iodo-tetrahydro-furan-3-yl ester
• 英文别名: [(2R,3S,4S,5S)-4,5-diacetyloxy-3-iodooxolan-2-yl]methyl acetate
• CAS: 74580-84-0
• 化学式: C₁₁H₁₅IO₇
• 分子量: 386.14
• InChiKey: FAWNXIGBGFDCOC-LMLFDSFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  乙酸酐 、 [(3aR,5R,6S,6aS)-6-iodo-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methyl acetate 在 硫酸 、 溶剂黄146 作用下， 反应 72.0h， 生成 Acetic acid (2S,3S,4S,5R)-2-acetoxy-5-acetoxymethyl-4-iodo-tetrahydro-furan-3-yl ester 、 Acetic acid (2R,3S,4S,5R)-2-acetoxy-5-acetoxymethyl-4-iodo-tetrahydro-furan-3-yl ester
  参考文献：
  名称：

  Nucleosides. 116. 1-(.beta.-D-Xylofuranosyl)-5-fluorocytosines with a leaving group on the 3' position. Potential double-barreled masked precursors of anticancer nucleosides

  摘要：

  Syntheses of five pairs of cytosine and 5-fluorocytosinexylofuranosyl nucleosides in which the 3'-hydroxyl group is replaced by Cl, Br, OMs, or OTs are described. Those xylosyl nucleosides with a good leaving group at the 3' position exhibit good inhibitory activity against L5178Y and P815 mouse leukemic cells in vitro at rather low concentrations, and like that of ara-C this cytotoxicity is reversed by 2'-deoxycytidine but not by thymidine. Xylosylcytosines are not active against ara-C resistant lines of L5178Y and P815 cells; however, the corresponding 5-fluorocytosine analogues exhibit significant cytotoxicity against these ara-C resistant leukemic cell lines, and this activity is reversed by thmidine but not by deoxycytidine. These data support the "double-barreled" masked precursor hypothesis in that xylosyl-5-fluorocytosines substituted at the 3' position by a good leaving group exhibit activity akin to that of ara-C in the ara-C sensitive lines, while these nucleosides act as 5-fluoropyrimidines in the ara-C resistant lines.

  DOI：

  10.1021/jm00184a006