(5E,7E)-(3S)-3β-t-butyldimethylsilyloxy-9,10-secocholesta-5,7,10(19)-trien-1α-yl 3-butenoate | 881032-35-5

• 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: (5E,7E)-(3S)-3β-t-butyldimethylsilyloxy-9,10-secocholesta-5,7,10(19)-trien-1α-yl 3-butenoate
• 英文别名: [(1S,3E,5R)-3-[(2E)-2-[(1R,3aS,7aR)-7a-methyl-1-[(2R)-6-methylheptan-2-yl]-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-5-[tert-butyl(dimethyl)silyl]oxy-2-methylidenecyclohexyl] but-3-enoate
• CAS: 881032-35-5
• 化学式: C₃₇H₆₂O₃Si
• 分子量: 582.983
• InChiKey: OAYPRVGEHQZWHZ-DDSUUPTASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.75
• 重原子数：
  41
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.76
• 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：

  (5E,7E)-(3S)-3β-t-butyldimethylsilyloxy-9,10-secocholesta-5,7,10(19)-trien-1α-yl 3-butenoate 在 Hoveyda-Grubbs catalyst second generation lithium aluminium tetrahydride 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 5.0h， 生成 (5E,7E)-(3S)-19-hydroxymethyl-9,10-secocholesta-5,7,10(19)-triene-1α,3β-diol
  参考文献：
  名称：

  Synthesis of γ- and δ-lactones from 1α-hydroxy-5,6-trans-vitamin D3 by ring-closing metathesis route and their reduction with metal hydrides

  摘要：

  New synthetic pathway towards 19-functionalized derivatives of 1 alpha-hydroxy-5,6-transvitamin D-3 was described. Ring-closing metathesis (RCM) of 1 alpha-hydroxy-5,6-trans-vitamin D-3 1-omega-alkenoates was a key-step. Hydride reduction of resulting lactones led to the new vitamin D-3 analogues. (c) 2007 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2007.03.005
• 作为产物：
  描述：

  乙烯基乙酸 、 (1S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-3-[2-[(1R,3aS,7aR)-1-((R)-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(E)-ylidene]-2-methylene-cyclohexanol 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以85%的产率得到(5E,7E)-(3S)-3β-t-butyldimethylsilyloxy-9,10-secocholesta-5,7,10(19)-trien-1α-yl 3-butenoate
  参考文献：
  名称：

  Synthesis of γ- and δ-lactones from 1α-hydroxy-5,6-trans-vitamin D3 by ring-closing metathesis route and their reduction with metal hydrides

  摘要：

  New synthetic pathway towards 19-functionalized derivatives of 1 alpha-hydroxy-5,6-transvitamin D-3 was described. Ring-closing metathesis (RCM) of 1 alpha-hydroxy-5,6-trans-vitamin D-3 1-omega-alkenoates was a key-step. Hydride reduction of resulting lactones led to the new vitamin D-3 analogues. (c) 2007 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2007.03.005

文献信息

• Application of Ring-Closing Metathesis to the Synthesis of 19-Functionalized Derivatives of 1α-Hydroxyvitamin D₃
  作者：Agnieszka Wojtkielewicz、Jacek W. Morzycki

  DOI：10.1021/ol052856k

  日期：2006.3.2

  The synthesis of the 19-functionalized derivative of vitamin D-3 based on ring-closing metathesis (RCM) is presented.