(25R)-6β-methoxy-25,26-epoxy-3α,5-cyclo-5α-cholestan-27-ol 27-methanesulphonate | 137369-52-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: (25R)-6β-methoxy-25,26-epoxy-3α,5-cyclo-5α-cholestan-27-ol 27-methanesulphonate
• CAS: 137369-52-9
• 化学式: C₂₉H₄₈O₅S
• 分子量: 508.763
• InChiKey: PAGGSRYBXHAPAQ-BIAFTAPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.82
• 重原子数：
  35.0
• 可旋转键数：
  9.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  65.13
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (25R)-6β-methoxy-25,26-epoxy-3α,5-cyclo-5α-cholestan-27-ol 27-methanesulphonate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以83%的产率得到(25R)-6β-methoxy-25,26-epoxy-27-fluoro-3α,5-cyclo-5α-cholestan
  参考文献：
  名称：

  Stereoselective synthesis of (25R)-26-fluoro-5-cholesten-3β,25-diol 3-acetate from methyl 3β-hydroxy-5-cholenoate

  摘要：

  A stereoselective synthesis of (25R)-26-fluoro-5-cholesten-3-beta,25-diol 3-acetate (1) from methyl 3-beta-hydroxy-5-cholenoate (2) is presented. Formation of the asymmetric center at C-25 was accomplished by application of the Sharpless epoxidation methodology from 6-beta-methoxy-3-alpha,5-cyclo-5-alpha-cholest-25(27)-en-26-ol (7). Substitution of the C-27 hydroxyl group of (25R)-6-beta-methoxy-3-alpha,5-cyclo-25,26-epoxy-5-alpha-cholestan-27-ol (8) by a fluorine atom, via mesylate derivative, and subsequent reduction of the oxirane ring with LiAIH4 afforded (25R)-6-beta-methoxy-26-fluoro-3-alpha,5-cyclo-5-alpha-cholestan-25-ol (16). Deprotection of the 3-beta-hydroxy-5(6)-en system in 16 with BF3.Et2O/acetic acid yielded the title compound 1.

  DOI：

  10.1016/s0022-1139(00)82344-1
• 作为产物：
  描述：

  Methanesulfonic acid (R)-4-((3aR,3bS,5aR,6R,8aS,8bS,10R,10aR)-10-methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-1-(2-trimethylsilanyl-oxiranyl)-pentyl ester 在 吡啶 、 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 正丁基锂 、 D-(-)-酒石酸二乙酯 、 四丁基氟化铵 、 水 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 33.0h， 生成 (25R)-6β-methoxy-25,26-epoxy-3α,5-cyclo-5α-cholestan-27-ol 27-methanesulphonate
  参考文献：
  名称：

  Stereoselective synthesis of (25R)-26-fluoro-5-cholesten-3β,25-diol 3-acetate from methyl 3β-hydroxy-5-cholenoate

  摘要：

  A stereoselective synthesis of (25R)-26-fluoro-5-cholesten-3-beta,25-diol 3-acetate (1) from methyl 3-beta-hydroxy-5-cholenoate (2) is presented. Formation of the asymmetric center at C-25 was accomplished by application of the Sharpless epoxidation methodology from 6-beta-methoxy-3-alpha,5-cyclo-5-alpha-cholest-25(27)-en-26-ol (7). Substitution of the C-27 hydroxyl group of (25R)-6-beta-methoxy-3-alpha,5-cyclo-25,26-epoxy-5-alpha-cholestan-27-ol (8) by a fluorine atom, via mesylate derivative, and subsequent reduction of the oxirane ring with LiAIH4 afforded (25R)-6-beta-methoxy-26-fluoro-3-alpha,5-cyclo-5-alpha-cholestan-25-ol (16). Deprotection of the 3-beta-hydroxy-5(6)-en system in 16 with BF3.Et2O/acetic acid yielded the title compound 1.

  DOI：

  10.1016/s0022-1139(00)82344-1