(E)-(2R,5S,7S)-10-(tert-Butyl-dimethyl-silanyloxy)-2,8-dimethyl-dec-8-ene-1,5,7-triol | 143236-67-3

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (E)-(2R,5S,7S)-10-(tert-Butyl-dimethyl-silanyloxy)-2,8-dimethyl-dec-8-ene-1,5,7-triol
• 英文别名: (E,2R,5S,7S)-10-[tert-butyl(dimethyl)silyl]oxy-2,8-dimethyldec-8-ene-1,5,7-triol
• CAS: 143236-67-3
• 化学式: C₁₈H₃₈O₄Si
• 分子量: 346.583
• InChiKey: WQWCNQADDJCVHA-UWKKETHDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.48
• 重原子数：
  23
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  69.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-(2R,5S,7S)-10-(tert-Butyl-dimethyl-silanyloxy)-2,8-dimethyl-dec-8-ene-1,5,7-triol 、 碘甲烷 在 tris(triphenylphosphine)ruthenium(II) chloride air 、 sodium hydride 作用下， 生成 tert-Butyl-[(E)-(S)-4-methoxy-5-((2S,5R,6R)-6-methoxy-5-methyl-tetrahydro-pyran-2-yl)-3-methyl-pent-2-enyloxy]-dimethyl-silane
  参考文献：
  名称：

  Synthetic investigations of rapamycin. 1. Synthesis of a C10-C21 fragment

  摘要：

  Phosphine oxide 2, representing the C-10-C21 portion of rapamycin, was stereoselectively synthesized and was demonstrated to undergo a Homer-Wittig reaction to form triene 25 as an 8:1 mixture of trans-cis isomers.

  DOI：

  10.1021/jo00045a007
• 作为产物：
  描述：

  (E,6S,9R)-1-[tert-butyl(dimethyl)silyl]oxy-6-hydroxy-10-[(4-methoxyphenyl)methoxy]-3,9-dimethyldec-2-en-4-one 在 sodium tetrahydroborate 、 二乙基甲氧基硼烷 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 生成 (E)-(2R,5S,7S)-10-(tert-Butyl-dimethyl-silanyloxy)-2,8-dimethyl-dec-8-ene-1,5,7-triol
  参考文献：
  名称：

  Synthetic investigations of rapamycin. 1. Synthesis of a C10-C21 fragment

  摘要：

  Phosphine oxide 2, representing the C-10-C21 portion of rapamycin, was stereoselectively synthesized and was demonstrated to undergo a Homer-Wittig reaction to form triene 25 as an 8:1 mixture of trans-cis isomers.

  DOI：

  10.1021/jo00045a007

文献信息

• Synthetic investigations of rapamycin. 1. Synthesis of a C10-C21 fragment
  作者：Stephanie D. Meyer、Tetsuo Miwa、Masashi Nakatsuka、Stuart L. Schreiber

  DOI：10.1021/jo00045a007

  日期：1992.9

  Phosphine oxide 2, representing the C-10-C21 portion of rapamycin, was stereoselectively synthesized and was demonstrated to undergo a Homer-Wittig reaction to form triene 25 as an 8:1 mixture of trans-cis isomers.