(3S,8S,9S,10R,13S,14S,17R)-17-((1S,2R,3R)-3-Allyloxy-2-methoxymethoxy-1,5-dimethyl-hexyl)-3-methoxymethoxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene | 140659-61-6

• 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: (3S,8S,9S,10R,13S,14S,17R)-17-((1S,2R,3R)-3-Allyloxy-2-methoxymethoxy-1,5-dimethyl-hexyl)-3-methoxymethoxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene
• CAS: 140659-61-6
• 化学式: C₃₄H₅₈O₅
• 分子量: 546.832
• InChiKey: JPVINYRLPBWFHB-PQTSLDGVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  39.0
• 可旋转键数：
  14.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  46.15
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (3S,8S,9S,10R,13S,14S,17R)-17-((1S,2R,3R)-3-Allyloxy-2-methoxymethoxy-1,5-dimethyl-hexyl)-3-methoxymethoxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene 在 sodium hydroxide 、 thexylborane 、 双氧水 、 potassium carbonate 、 pyridinium chlorochromate 作用下， 以 甲醇 为溶剂， 生成 (22R,23R)-3β,22,23-trihydroxycholest-5-ene 3,22-dimethoxymethyl ether
  参考文献：
  名称：

  Stereocontrol of three contiguous chiral centers of brassinosteroid side chain by using .alpha.-alkoxy organoleads

  摘要：

  The reaction of steroidal aldehyde 2 with chiral alpha-methoxyorganolead (S)-3 in the presence of TiCl4 gave the Cram-syn product 4, a precursor of 28-norbrassinolide, in 90% yield as a single stereoisomer. A kinetic resolution was observed in the TiCl4 mediated reaction of 2 with (+/-)-3; again 4 was produced in 99% yield as a single isomer.

  DOI：

  10.1021/jo00037a002
• 作为产物：
  描述：

  (1-Allyloxy-3-methyl-butyl)-tributyl-plumbane 在 oxonium 、 四氯化钛 作用下， 反应 12.0h， 生成 (3S,8S,9S,10R,13S,14S,17R)-17-((1S,2R,3R)-3-Allyloxy-2-methoxymethoxy-1,5-dimethyl-hexyl)-3-methoxymethoxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene
  参考文献：
  名称：

  Stereocontrol of three contiguous chiral centers of brassinosteroid side chain by using .alpha.-alkoxy organoleads

  摘要：

  The reaction of steroidal aldehyde 2 with chiral alpha-methoxyorganolead (S)-3 in the presence of TiCl4 gave the Cram-syn product 4, a precursor of 28-norbrassinolide, in 90% yield as a single stereoisomer. A kinetic resolution was observed in the TiCl4 mediated reaction of 2 with (+/-)-3; again 4 was produced in 99% yield as a single isomer.

  DOI：

  10.1021/jo00037a002