(22R,23R)-3β,22,23-trihydroxycholest-5-ene 3,22-dimethoxymethyl ether | 93344-73-1

• 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: (22R,23R)-3β,22,23-trihydroxycholest-5-ene 3,22-dimethoxymethyl ether
• 英文别名: (2S,3R,4R)-3-(methoxymethoxy)-2-[(3S,8S,9S,10R,13S,14S,17R)-3-(methoxymethoxy)-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-methylheptan-4-ol
• CAS: 93344-73-1
• 化学式: C₃₁H₅₄O₅
• 分子量: 506.767
• InChiKey: LWVUJADOKWAOKY-NVBMTMDYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.59
• 重原子数：
  36.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  57.15
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (22R,23R)-3β,22,23-trihydroxycholest-5-ene 3,22-dimethoxymethyl ether 在 盐酸 、 甲醇 作用下， 以80%的产率得到(22R,23R)-3β,22,23-trihydroxycholest-5-ene
  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：

  3β-(t-butyldimethylsilyloxy)-23,24-dinorchol-5-enaldehyde 在 sodium hydroxide 、 thexylborane 、 oxonium 、 双氧水 、 四氯化钛 、 potassium carbonate 、 pyridinium chlorochromate 作用下， 以 甲醇 为溶剂， 反应 12.0h， 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

文献信息

• Takatsuto, Suguru; Ikekawa, Nobuo, Chemical and pharmaceutical bulletin, 1987, vol. 35, # 7, p. 3006 - 3010
  作者：Takatsuto, Suguru、Ikekawa, Nobuo

  DOI：——

  日期：——
• TAKATSUTO, SUGURU;IKEKAWA, NOBUO, CHEM. AND PHARM. BULL., 35,(1987) N 7, 3006-3010
  作者：TAKATSUTO, SUGURU、IKEKAWA, NOBUO

  DOI：——

  日期：——