(5S,9R,10S,13S)-15-(tert-butyldiphenylsilyloxy)-13-hydroxy-labd-7-en-11-one | 263763-63-9

• 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: (5S,9R,10S,13S)-15-(tert-butyldiphenylsilyloxy)-13-hydroxy-labd-7-en-11-one
• 英文别名: (3S)-1-[(1S,4aS,8aS)-2,5,5,8a-tetramethyl-1,4,4a,6,7,8-hexahydronaphthalen-1-yl]-5-[tert-butyl(diphenyl)silyl]oxy-3-hydroxy-3-methylpentan-1-one
• CAS: 263763-63-9
• 化学式: C₃₆H₅₂O₃Si
• 分子量: 560.893
• InChiKey: MFHSPYUTGFXKNK-KDDXCEFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.46
• 重原子数：
  40
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 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：

  (5S,9R,10S,13S)-15-(tert-butyldiphenylsilyloxy)-13-hydroxy-labd-7-en-11-one 以 水 、 苯 为溶剂， 反应 2.0h， 生成 (S)-5-(tert-Butyl-diphenyl-silanyloxy)-3-hydroxy-1-((3S,4aS,8aS)-3-hydroxy-2,5,5,8a-tetramethyl-3,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl)-3-methyl-pentan-1-one
  参考文献：
  名称：

  Studies on a forskolin ring C forming reaction

  摘要：

  Results are reported that indicate that the rearrangement of hydroxy epoxide 2a to dihydropyran 3 which occurs with retention of configuration at C-8 proceeds either via a carbocation intermediate or by two successive substitution reactions, both with inversion of configuration, (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01957-7
• 作为产物：
  描述：

  (E)-(tert-butyl)(4-iodo-3-methylbut-3-enyloxy)diphenylsilane 在 重铬酸吡啶 、 samarium diiodide 、 tert-butyl hydroperoxide (80 percent in di-tert-butyl peroxide) 、 vanadyl acetylacetonate 、 叔丁基锂 、 potassium carbonate 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 11.0h， 生成 (5S,9R,10S,13S)-15-(tert-butyldiphenylsilyloxy)-13-hydroxy-labd-7-en-11-one
  参考文献：
  名称：

  Synthesis of an advanced forskolin intermediate

  摘要：

  The 8,13-epoxylabdane derivative rac-19 was prepared in eight steps commencing from (E,E)-farnesol (8). Key reactions are the formation of 7 from drimenal (9b) and 6, Sharpless I epoxidation (7 --> 11), epoxy alcohol oxidation (11 --> 16), reductive epoxide cleavage (16 --> 15), peracid epoxidation (15 --> 18), and the trimethylsilyl triflate-mediated conversion of 18 into 19.

  DOI：

  10.1016/s0040-4020(01)86324-9

文献信息

• Forskolin Studies
  作者：Dirk Behnke、Lothar Hennig、Matthias Findeisen、Peter Welzel、Dietrich Müller、Michael Thormann、Hans-Jörg Hofmann

  DOI：10.1016/s0040-4020(00)00005-3

  日期：2000.2

  reagent is introduced which allowed synthesis of an advanced and optically active forskolin intermediate in a very efficient way. In addition, docking experiments that are based on X-ray results indicate that there might exist forskolin analogues with improved properties as far as binding to adenylyl cyclases and synthetic accessibility are concerned.

  引入了一种新的亲核类异戊二烯C 5试剂，该试剂可以以非常有效的方式合成高级的和光学活性的佛司可林中间体。此外，基于X射线结果的对接实验表明，就与腺苷酸环化酶的结合和合成可及性而言，可能存在具有改进性质的毛喉素类似物。
• Synthesis of an advanced forskolin intermediate
  作者：Stefan Bick、Silke Zimmermann、Heike Meuer、William S. Sheldrick、Peter Welzel

  DOI：10.1016/s0040-4020(01)86324-9

  日期：1993.3

  The 8,13-epoxylabdane derivative rac-19 was prepared in eight steps commencing from (E,E)-farnesol (8). Key reactions are the formation of 7 from drimenal (9b) and 6, Sharpless I epoxidation (7 --> 11), epoxy alcohol oxidation (11 --> 16), reductive epoxide cleavage (16 --> 15), peracid epoxidation (15 --> 18), and the trimethylsilyl triflate-mediated conversion of 18 into 19.
• Studies on a forskolin ring C forming reaction
  作者：Stefan Hamm、Silke Zimmermann、Lothar Hennig、Dietrich Müller、Peter Welzel

  DOI：10.1016/s0040-4039(99)01957-7

  日期：1999.12

  Results are reported that indicate that the rearrangement of hydroxy epoxide 2a to dihydropyran 3 which occurs with retention of configuration at C-8 proceeds either via a carbocation intermediate or by two successive substitution reactions, both with inversion of configuration, (C) 1999 Elsevier Science Ltd. All rights reserved.