(((2S,4S,5'R,6aR,6bS,8aS,8bR,9S,10R,11aS,12aS,12bR)-2-(allyloxy)-5',6a,8a,9-tetramethyldocosahydrospiro[naphtho[2',1':4,5]indeno[2,1-b]furan-10,2'-pyran]-4-yl)oxy)(tert-butyl)diphenylsilane | 1381876-15-8

• 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: (((2S,4S,5'R,6aR,6bS,8aS,8bR,9S,10R,11aS,12aS,12bR)-2-(allyloxy)-5',6a,8a,9-tetramethyldocosahydrospiro[naphtho[2',1':4,5]indeno[2,1-b]furan-10,2'-pyran]-4-yl)oxy)(tert-butyl)diphenylsilane
• CAS: 1381876-15-8
• 化学式: C₄₆H₆₆O₄Si
• 分子量: 711.113
• InChiKey: SKSSRVXIYDDXNM-UFIRYIOESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.56
• 重原子数：
  51.0
• 可旋转键数：
  7.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (((2S,4S,5'R,6aR,6bS,8aS,8bR,9S,10R,11aS,12aS,12bR)-2-(allyloxy)-5',6a,8a,9-tetramethyldocosahydrospiro[naphtho[2',1':4,5]indeno[2,1-b]furan-10,2'-pyran]-4-yl)oxy)(tert-butyl)diphenylsilane 在 perchloric acid on silica gel 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以89%的产率得到(2S,4S,5'R,6aR,6bS,8aS,8bR,9S,10R,11aS,12aS,12bR)-2-(allyloxy)-5',6a,8a,9-tetramethyldocosahydrospiro[naphtho[2',1':4,5]indeno[2,1-b]furan-10,2'-pyran]-4-ol
  参考文献：
  名称：

  An efficient and recyclable catalyst for the cleavage of tert-butyldiphenylsilyl ethers

  摘要：

  An efficient, chemoselective, and environment-friendly method for the deprotection of tert-butyldiphenylsilyl ethers mediated by triflic acid supported on silica gel is reported. A wide range of tert-butyldiphenylsilyl ethers derived from carbohydrate and saponin residues can be smoothly cleaved in the presence of various types of other protecting groups in good to excellent yields in acetonitrile. This heterogeneous reaction does not require aqueous workup, and the supported catalyst can be readily recycled. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2012.02.021
• 作为产物：
  描述：

  (25R)-3β-tert-butyldiphenylsilyloxy-spirostan-5-ene 在 四丁基碘化铵 、 sodium hydride 、 diborane(6) 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.5h， 生成 (((2S,4S,5'R,6aR,6bS,8aS,8bR,9S,10R,11aS,12aS,12bR)-2-(allyloxy)-5',6a,8a,9-tetramethyldocosahydrospiro[naphtho[2',1':4,5]indeno[2,1-b]furan-10,2'-pyran]-4-yl)oxy)(tert-butyl)diphenylsilane
  参考文献：
  名称：

  An efficient and recyclable catalyst for the cleavage of tert-butyldiphenylsilyl ethers

  摘要：

  An efficient, chemoselective, and environment-friendly method for the deprotection of tert-butyldiphenylsilyl ethers mediated by triflic acid supported on silica gel is reported. A wide range of tert-butyldiphenylsilyl ethers derived from carbohydrate and saponin residues can be smoothly cleaved in the presence of various types of other protecting groups in good to excellent yields in acetonitrile. This heterogeneous reaction does not require aqueous workup, and the supported catalyst can be readily recycled. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2012.02.021