(7SR,13SR)-15-(tert-butyldiphenylsilyloxy)-13-hydroxy-7-trifluoracetoxy-rac-labd-8-en-11-one

• 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: (7SR,13SR)-15-(tert-butyldiphenylsilyloxy)-13-hydroxy-7-trifluoracetoxy-rac-labd-8-en-11-one
• 英文别名: [(2S,4aS,8aS)-4-[(3S)-5-[tert-butyl(diphenyl)silyl]oxy-3-hydroxy-3-methylpentanoyl]-3,4a,8,8-tetramethyl-1,2,5,6,7,8a-hexahydronaphthalen-2-yl] 2,2,2-trifluoroacetate
• 化学式: C₃₈H₅₁F₃O₅Si
• 分子量: 672.901
• InChiKey: UVUMAAPXBVHXHK-JKUGMWFDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.69
• 重原子数：
  47
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (7SR,13SR)-15-(tert-butyldiphenylsilyloxy)-13-hydroxy-7-trifluoracetoxy-rac-labd-8-en-11-one 以 水 为溶剂， 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：

  反式,反式-金合欢醇 在 重铬酸吡啶 、 samarium diiodide 、 tert-butyl hydroperoxide (80 percent in di-tert-butyl peroxide) 、 vanadyl acetylacetonate 、 叔丁基锂 、 氟磺酸 、 potassium carbonate 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 18.0h， 生成 (7SR,13SR)-15-(tert-butyldiphenylsilyloxy)-13-hydroxy-7-trifluoracetoxy-rac-labd-8-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

• 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.