methyl (E)-6β-methoxy-3α,5α-cyclochol-22-en-24-oate | 56259-12-2

• 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: methyl (E)-6β-methoxy-3α,5α-cyclochol-22-en-24-oate
• 英文别名: methyl (E,4R)-4-[(1S,2R,5R,7R,8R,10S,11S,14R,15R)-8-methoxy-2,15-dimethyl-14-pentacyclo[8.7.0.02,7.05,7.011,15]heptadecanyl]pent-2-enoate
• CAS: 56259-12-2
• 化学式: C₂₆H₄₀O₃
• 分子量: 400.602
• InChiKey: ABZBRFRNSNVMHQ-SFOGAIDISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (E)-6β-methoxy-3α,5α-cyclochol-22-en-24-oate 在 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以89%的产率得到(E)-6β-methoxy-3α,5α-cyclochol-22-en-24-ol
  参考文献：
  名称：

  Asymmetric isopropylation of steroidal 24-aldehydes for the synthesis of 24(R)-hydroxycholesterol

  摘要：

  The chiral beta-amino alcohols-catalyzed addition of diisopropylzinc to steroidal 24-aldehydes successfully provided 24(R)-hydroxycholesterols in good yields with high diastereoselectivities, which are synthetic intermediates of 1 alpha,24(R)-dihydroxyvitamin D-3 (1). alpha,beta-Unsaturated steroidal aldehydes were found to give the corresponding isopropylated adducts in much higher yields (up to 91%) than those of saturated steroidal aldehydes.

  DOI：

  10.1016/0957-4166(95)00073-x
• 作为产物：
  描述：

  6β-甲氧基-3α，5-环-5α-孕烷-20α-甲醛 、 甲氧羰基亚甲基三苯基正膦 以 甲苯 为溶剂， 反应 24.0h， 以5.86 g的产率得到methyl (E)-6β-methoxy-3α,5α-cyclochol-22-en-24-oate
  参考文献：
  名称：

  Asymmetric isopropylation of steroidal 24-aldehydes for the synthesis of 24(R)-hydroxycholesterol

  摘要：

  The chiral beta-amino alcohols-catalyzed addition of diisopropylzinc to steroidal 24-aldehydes successfully provided 24(R)-hydroxycholesterols in good yields with high diastereoselectivities, which are synthetic intermediates of 1 alpha,24(R)-dihydroxyvitamin D-3 (1). alpha,beta-Unsaturated steroidal aldehydes were found to give the corresponding isopropylated adducts in much higher yields (up to 91%) than those of saturated steroidal aldehydes.

  DOI：

  10.1016/0957-4166(95)00073-x

文献信息

• Asymmetric isopropylation of steroidal 24-aldehydes for the synthesis of 24(R)-hydroxycholesterol
  作者：Makoto Okamoto、Masayasu Tabe、Takao Fujii、Toshio Tanaka

  DOI：10.1016/0957-4166(95)00073-x

  日期：1995.3

  The chiral beta-amino alcohols-catalyzed addition of diisopropylzinc to steroidal 24-aldehydes successfully provided 24(R)-hydroxycholesterols in good yields with high diastereoselectivities, which are synthetic intermediates of 1 alpha,24(R)-dihydroxyvitamin D-3 (1). alpha,beta-Unsaturated steroidal aldehydes were found to give the corresponding isopropylated adducts in much higher yields (up to 91%) than those of saturated steroidal aldehydes.