[(1R,3aR,4S,7aR)-1-[(E,2R,5S)-6-hydroxy-5,6-dimethylhept-3-en-2-yl]-7a-methyl-1,2,3,3a,4,5,6,7-octahydroinden-4-yl] benzoate | 138079-57-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: [(1R,3aR,4S,7aR)-1-[(E,2R,5S)-6-hydroxy-5,6-dimethylhept-3-en-2-yl]-7a-methyl-1,2,3,3a,4,5,6,7-octahydroinden-4-yl] benzoate
• CAS: 138079-57-9
• 化学式: C₂₆H₃₈O₃
• 分子量: 398.586
• InChiKey: SSDCUWAYRHKOEL-AHPQBHDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [(1R,3aR,4S,7aR)-1-[(E,2R,5S)-6-hydroxy-5,6-dimethylhept-3-en-2-yl]-7a-methyl-1,2,3,3a,4,5,6,7-octahydroinden-4-yl] benzoate 在 lithium aluminium tetrahydride 、 甲基锂 、 N,N-二异丙基乙胺 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 33.0h， 生成 25-羟基二氢速甾醇(2)
  参考文献：
  名称：

  25-hydroxydihydrotachysterol2 an innovative synthesis of a key metabolite of dihydrotachysterol2

  摘要：

  A new synthesis of 25-hydroxydihydrotachysterol2 is described The hydroxylated side-chain is constructed stereoselectively using a chiral Wittig reagent. The A-ring synthon is introduced utilising the Wittig-Horner method as developed by Lythgoe et al. The preparation of the metabolite is carried out in 18 steps.

  DOI：

  10.1016/s0040-4020(01)85618-0
• 作为产物：
  描述：

  维生素D2 在 吡啶 、 4-二甲氨基吡啶 、 氢氧化钾 、 sodium tetrahydroborate 、 甲基锂 、 臭氧 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 82.17h， 生成 [(1R,3aR,4S,7aR)-1-[(E,2R,5S)-6-hydroxy-5,6-dimethylhept-3-en-2-yl]-7a-methyl-1,2,3,3a,4,5,6,7-octahydroinden-4-yl] benzoate
  参考文献：
  名称：

  25-hydroxydihydrotachysterol2 an innovative synthesis of a key metabolite of dihydrotachysterol2

  摘要：

  A new synthesis of 25-hydroxydihydrotachysterol2 is described The hydroxylated side-chain is constructed stereoselectively using a chiral Wittig reagent. The A-ring synthon is introduced utilising the Wittig-Horner method as developed by Lythgoe et al. The preparation of the metabolite is carried out in 18 steps.

  DOI：

  10.1016/s0040-4020(01)85618-0

文献信息

• A short and efficient synthesis of DE-A,B(22E,24S)-8β-(benzoyloxy)-25-hydroxyergost-22-ene a valuable intermediate in the total synthesis of 25-hydroxylated vitamin D2-metabolites
  作者：Jaap C. Hanekamp、Rob Boer Rookhuizen、Henry L.A.v.d. Heuvel、Hendrik J.T. Bos、Lambert Brandsma

  DOI：10.1016/s0040-4039(00)92396-7

  日期：1991.9

  The titel compound was synthesised in 8 steps starting from vitamin D2. The side-chain was constructed using a chiral, stereoselective Wittig-reagent.
• 25-hydroxydihydrotachysterol2 an innovative synthesis of a key metabolite of dihydrotachysterol2
  作者：Jaap C. Hanekamp、Rob Boer Rookhuizen、Hendrik J.T. Bos、Lambert Brandsma

  DOI：10.1016/s0040-4020(01)85618-0

  日期：1992.1

  A new synthesis of 25-hydroxydihydrotachysterol2 is described The hydroxylated side-chain is constructed stereoselectively using a chiral Wittig reagent. The A-ring synthon is introduced utilising the Wittig-Horner method as developed by Lythgoe et al. The preparation of the metabolite is carried out in 18 steps.