Benzoic acid (1S,2R,3R,4S,5R,6S)-2,3,4-tris-benzyloxy-6-(1-ethoxy-ethoxy)-5-fluoro-cyclohexyl ester | 1054658-35-3

• 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 (1S,2R,3R,4S,5R,6S)-2,3,4-tris-benzyloxy-6-(1-ethoxy-ethoxy)-5-fluoro-cyclohexyl ester
• 英文别名: [(1S,2S,3R,4S,5R,6R)-2-(1-ethoxyethoxy)-3-fluoro-4,5,6-tris(phenylmethoxy)cyclohexyl] benzoate
• CAS: 1054658-35-3
• 化学式: C₃₈H₄₁FO₇
• 分子量: 628.738
• InChiKey: HSBVIIAYBHUOMG-XVTFUXLLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  46
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Benzoic acid (1S,2R,3R,4S,5R,6S)-2,3,4-tris-benzyloxy-6-(1-ethoxy-ethoxy)-5-fluoro-cyclohexyl ester 在 四氮唑 、 二异丙基铵盐四氮唑 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 生成 Hexadecanoic acid (R)-2-{benzyloxy-[(1S,2R,3R,4S,5R,6S)-2,3,4-tris-benzyloxy-6-(1-ethoxy-ethoxy)-5-fluoro-cyclohexyloxy]-phosphanyloxy}-1-hexadecanoyloxymethyl-ethyl 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 CPI is inactive as is the simplified analogue 24 of FPI in which the phosphatidic acid moiety has been replaced by an octadecyl group.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
• 作为产物：
  描述：

  D-4,5,6-Tri-O-benzyl-3-deoxy-3-fluoro-1,2-O-isopropylidene-myo-inositol 在 盐酸 、 camphor-10-sulfonic acid 吡啶 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 21.0h， 生成 Benzoic acid (1S,2R,3R,4S,5R,6S)-2,3,4-tris-benzyloxy-6-(1-ethoxy-ethoxy)-5-fluoro-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