(17E)-1α-tert-butyldimethylsilyloxy-20-[3-(methyloxycarbonyl)phenyl]-17,20-didehydro-21,22,23,24,25,26,27-heptanorvitamin D₃ tert-butyldimethylsilyl ether | 307318-51-0

• 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: (17E)-1α-tert-butyldimethylsilyloxy-20-[3-(methyloxycarbonyl)phenyl]-17,20-didehydro-21,22,23,24,25,26,27-heptanorvitamin D₃ tert-butyldimethylsilyl ether
• 英文别名: methyl 3-[(E)-[(3aS,4E,7aS)-4-[(2Z)-2-[(3S,5R)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-methylidenecyclohexylidene]ethylidene]-7a-methyl-2,3,3a,5,6,7-hexahydroinden-1-ylidene]methyl]benzoate
• CAS: 307318-51-0
• 化学式: C₄₀H₆₂O₄Si₂
• 分子量: 663.101
• InChiKey: PLXVXFXRZSZJOC-UOLUXEHTSA-N

物化性质

• 沸点：
  656.5±55.0 °C(predicted)
• 密度：
  1.02±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  11.44
• 重原子数：
  46
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (17E)-1α-tert-butyldimethylsilyloxy-20-[3-(methyloxycarbonyl)phenyl]-17,20-didehydro-21,22,23,24,25,26,27-heptanorvitamin D₃ tert-butyldimethylsilyl ether 在 四丁基氟化铵 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 26.75h， 生成 (17E)-1α-20-[3-(dimethylhydroxymethyl)phenyl]-17,20-didehydro-21,22,23,24,25,26,27-heptanorvitamin D₃
  参考文献：
  名称：

  Synthesis of New Aromatic (C17−C20)-Locked Side-Chain Analogues of Calcitriol (1α,25-Dihydroxyvitamin D₃)^,1

  摘要：

  The synthesis of four new analogues of calcitriol (1 alpha ,25-(OH)(2)-D-3) possessing aromatic and conjugated double bond units at the side chain are described. The triene system is introduced using the Lythgoe-Hoffmann La Roche convergent Wittig-Horner approach. The key steps in the preparation of the requisite upper fragments are the introduction of the side chain with the E-conjugated aromatic system and its photochemical conversion to the Z counterpart.

  DOI：

  10.1021/jo000579j
• 作为产物：
  描述：

  8β-tert-butyldimethylsilyloxy-(17E)-{1-[3-(methyloxycarbonyl)phenyl]methylidene}-de-A,B-androstane 在 重铬酸吡啶 、 正丁基锂 、 氢氟酸 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 乙腈 为溶剂， 反应 17.0h， 生成 (17E)-1α-tert-butyldimethylsilyloxy-20-[3-(methyloxycarbonyl)phenyl]-17,20-didehydro-21,22,23,24,25,26,27-heptanorvitamin D₃ tert-butyldimethylsilyl ether
  参考文献：
  名称：

  Synthesis of New Aromatic (C17−C20)-Locked Side-Chain Analogues of Calcitriol (1α,25-Dihydroxyvitamin D₃)^,1

  摘要：

  The synthesis of four new analogues of calcitriol (1 alpha ,25-(OH)(2)-D-3) possessing aromatic and conjugated double bond units at the side chain are described. The triene system is introduced using the Lythgoe-Hoffmann La Roche convergent Wittig-Horner approach. The key steps in the preparation of the requisite upper fragments are the introduction of the side chain with the E-conjugated aromatic system and its photochemical conversion to the Z counterpart.

  DOI：

  10.1021/jo000579j

文献信息

• Synthesis of New Aromatic (C17−C20)-Locked Side-Chain Analogues of Calcitriol (1α,25-Dihydroxyvitamin D₃)^,¹
  作者：Ana Fernández-Gacio、Cristian Vitale、Antonio Mouriño

  DOI：10.1021/jo000579j

  日期：2000.10.1

  The synthesis of four new analogues of calcitriol (1 alpha ,25-(OH)(2)-D-3) possessing aromatic and conjugated double bond units at the side chain are described. The triene system is introduced using the Lythgoe-Hoffmann La Roche convergent Wittig-Horner approach. The key steps in the preparation of the requisite upper fragments are the introduction of the side chain with the E-conjugated aromatic system and its photochemical conversion to the Z counterpart.