Benzoic acid (1R,2R,3R,4S,5S,6S)-2,3,4-tris-benzyloxy-5-fluoro-6-hydroxy-cyclohexyl ester | 1054622-33-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Benzoic acid (1R,2R,3R,4S,5S,6S)-2,3,4-tris-benzyloxy-5-fluoro-6-hydroxy-cyclohexyl ester
• 英文别名: [(1R,2S,3S,4S,5R,6R)-3-fluoro-2-hydroxy-4,5,6-tris(phenylmethoxy)cyclohexyl] benzoate
• CAS: 1054622-33-1
• 化学式: C₃₄H₃₃FO₆
• 分子量: 556.631
• InChiKey: GDQPRVFYULSVKF-JTKPTSOWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  41
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Benzoic acid (1R,2R,3R,4S,5S,6S)-2,3,4-tris-benzyloxy-5-fluoro-6-hydroxy-cyclohexyl ester 在 camphor-10-sulfonic acid potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 (1S,2S,3R,4S,5R,6S)-2,3,4-Tris-benzyloxy-6-(1-ethoxy-ethoxy)-5-fluoro-cyclohexanol
  参考文献：
  名称：

  Synthesis and Biological Activity of the D-3-Deoxy-3-fluoro and D-3-Chloro-3-deoxy Analogs of Phosphatidylinositol

  摘要：

  The naturally occurring inositol derivative, L-quebrachitol (1), serves as starting material for the synthesis of D-3-deoxy-3-fluoro- and D-3-chloro-3-deoxy-myo-inositol (4, 28). Their transformation into the title compounds 22 and 40 (abbreviated as FPI and CPI, respectively) is accomplished by benzylation of all hydroxyl groups but OH-1 to which the phosphatidic acid side chain is subsequently attached using the phosphoramidite protocol, and hydrogenolytic deprotection. Compounds 4 and 28, as reported earlier, exhibit moderate and high selectivity, respectively, in the growth inhibition of v-sis transformed vs wild type murine NIH 3T3 cells if myo-inositol is absent but are inactive in the presence of physiological inositol levels. On the other hand, FPI possesses a nearly 2 orders of magnitude higher activity but no selectivity both in the absence or presence of myo-inositol. CPI is inactive as is the simplified analogue 24 of FPI in which the phosphatidic acid moiety has been replaced by an octadecyl group.

  DOI：

  10.1021/jo00084a010
• 作为产物：
  描述：

  (1S,2S,4R,5S)-6-fluorocyclohexane-1,2,3,4,5-pentol 在 盐酸 、 camphor-10-sulfonic acid 吡啶 、 sodium hydride 、 乙酰氯 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.0h， 生成 Benzoic acid (1R,2R,3R,4S,5S,6S)-2,3,4-tris-benzyloxy-5-fluoro-6-hydroxy-cyclohexyl ester
  参考文献：
  名称：

  Synthesis and Biological Activity of the D-3-Deoxy-3-fluoro and D-3-Chloro-3-deoxy Analogs of Phosphatidylinositol

  摘要：

  The naturally occurring inositol derivative, L-quebrachitol (1), serves as starting material for the synthesis of D-3-deoxy-3-fluoro- and D-3-chloro-3-deoxy-myo-inositol (4, 28). Their transformation into the title compounds 22 and 40 (abbreviated as FPI and CPI, respectively) is accomplished by benzylation of all hydroxyl groups but OH-1 to which the phosphatidic acid side chain is subsequently attached using the phosphoramidite protocol, and hydrogenolytic deprotection. Compounds 4 and 28, as reported earlier, exhibit moderate and high selectivity, respectively, in the growth inhibition of v-sis transformed vs wild type murine NIH 3T3 cells if myo-inositol is absent but are inactive in the presence of physiological inositol levels. On the other hand, FPI possesses a nearly 2 orders of magnitude higher activity but no selectivity both in the absence or presence of myo-inositol. CPI is inactive as is the simplified analogue 24 of FPI in which the phosphatidic acid moiety has been replaced by an octadecyl group.

  DOI：

  10.1021/jo00084a010

文献信息

• Synthesis and Biological Activity of the D-3-Deoxy-3-fluoro and D-3-Chloro-3-deoxy Analogs of Phosphatidylinositol
  作者：Alan P. Kozikowski、Garth Powis、Abdul H. Fauq、Werner Tuckmantel、Alfred Gallegos

  DOI：10.1021/jo00084a010

  日期：1994.3

  The naturally occurring inositol derivative, L-quebrachitol (1), serves as starting material for the synthesis of D-3-deoxy-3-fluoro- and D-3-chloro-3-deoxy-myo-inositol (4, 28). Their transformation into the title compounds 22 and 40 (abbreviated as FPI and CPI, respectively) is accomplished by benzylation of all hydroxyl groups but OH-1 to which the phosphatidic acid side chain is subsequently attached using the phosphoramidite protocol, and hydrogenolytic deprotection. Compounds 4 and 28, as reported earlier, exhibit moderate and high selectivity, respectively, in the growth inhibition of v-sis transformed vs wild type murine NIH 3T3 cells if myo-inositol is absent but are inactive in the presence of physiological inositol levels. On the other hand, FPI possesses a nearly 2 orders of magnitude higher activity but no selectivity both in the absence or presence of myo-inositol. CPI is inactive as is the simplified analogue 24 of FPI in which the phosphatidic acid moiety has been replaced by an octadecyl group.