2-[(E)-(1R,4S,6S)-4,9-Bis-(tert-butyl-dimethyl-silanyloxy)-6-methoxy-1,7-dimethyl-non-7-enyl]-[1,3]dithiolane | 143236-71-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二硫杂环戊烷
• 英文名称: 2-[(E)-(1R,4S,6S)-4,9-Bis-(tert-butyl-dimethyl-silanyloxy)-6-methoxy-1,7-dimethyl-non-7-enyl]-[1,3]dithiolane
• 英文别名: tert-butyl-[(E,4S,6S,9R)-6-[tert-butyl(dimethyl)silyl]oxy-9-(1,3-dithiolan-2-yl)-4-methoxy-3-methyldec-2-enoxy]-dimethylsilane
• CAS: 143236-71-9
• 化学式: C₂₇H₅₆O₃S₂Si₂
• 分子量: 549.043
• InChiKey: GSANBUOJPZJKRP-PNKZNXOOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.97
• 重原子数：
  34
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  78.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[(E)-(1R,4S,6S)-4,9-Bis-(tert-butyl-dimethyl-silanyloxy)-6-methoxy-1,7-dimethyl-non-7-enyl]-[1,3]dithiolane 在 吡啶 、 氟化氢吡啶 、 [双(三氟乙酰氧基)碘]苯 作用下， 以 四氢呋喃 为溶剂， 生成 (E)-(4S,6S,9R)-6-(tert-Butyl-dimethyl-silanyloxy)-4,10,10-trimethoxy-3,9-dimethyl-dec-2-en-1-ol
  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：

  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 在 2,6-二甲基吡啶 、 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 生成 2-[(E)-(1R,4S,6S)-4,9-Bis-(tert-butyl-dimethyl-silanyloxy)-6-methoxy-1,7-dimethyl-non-7-enyl]-[1,3]dithiolane
  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.