3-chloro-3-deoxy-1,2-O-isopropylidene-α-D-glucofuranose | 62255-75-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-chloro-3-deoxy-1,2-O-isopropylidene-α-D-glucofuranose
• 英文别名: (1R)-1-[(3aR,5R,6S,6aS)-6-chloro-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]ethane-1,2-diol
• CAS: 62255-75-8
• 化学式: C₉H₁₅ClO₅
• 分子量: 238.668
• InChiKey: RCXMKFMEMPCWIS-OZRXBMAMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.18
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  68.15
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3-chloro-3-deoxy-1,2-O-isopropylidene-α-D-glucofuranose 在 吡啶 、 sodium tetrahydroborate 、 sodium periodate 作用下， 以 乙醇 为溶剂， 反应 45.0h， 生成 Acetic acid (3aR,5R,6S,6aS)-6-chloro-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl 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
• 作为产物：
  描述：

  3-氯-3-脱氧-1,2:5,6-二异亚丙基-alpha-d-呋喃葡萄糖 在 硫酸 作用下， 以 甲醇 为溶剂， 反应 8.0h， 以89%的产率得到3-chloro-3-deoxy-1,2-O-isopropylidene-α-D-glucofuranose
  参考文献：
  名称：

  一系列脱氧和脱氧氟-α-d-“吡喃葡萄糖基”磷酸酯的合成和水解

  摘要：

  摘要描述了三种脱氧-α-d-“吡喃葡萄糖基”磷酸酯和一系列双脱氧单氟-和双脱氧二氟-α-d-吡喃葡萄糖基磷酸酯的合成。测定其酸催化水解的速率常数。已显示糖环中的脱氧可将水解速率提高至先前对一系列苯基脱氧d-“吡喃葡萄糖苷”进行酸催化水解所见的程度[Mega and Matsushima，J. Biochem。东京，94（1983）1637]。这表明这两个反应的过渡态基本相同。通过确定一系列脱氧和脱氧氟取代的6-脱氧-6-氟-α-d-葡萄糖基吡喃糖基磷酸酯的水解速率，可证明对糖环的取代基作用具有可预测的加性，并且本质上主要是电子的，

  DOI：

  10.1016/0008-6215(89)80055-2

文献信息

• WITHERS, STEPHEN G.;PERCIVAL, M. DAVID;STREET, IAN P., CARBOHYDR. RES., 187,(1989) N, C. 43-66
  作者：WITHERS, STEPHEN G.、PERCIVAL, M. DAVID、STREET, IAN P.

  DOI：——

  日期：——