(2S,3S,4R,5R,6S,10S,11R,12S)-5,13-bis[[tert-butyl(dimethyl)silyl]oxy]-11-(methoxymethoxy)-3-[(4-methoxyphenyl)methoxy]-2,4,6,8,10,12-hexamethyltridec-8-en-1-ol

• 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,3S,4R,5R,6S,10S,11R,12S)-5,13-bis[[tert-butyl(dimethyl)silyl]oxy]-11-(methoxymethoxy)-3-[(4-methoxyphenyl)methoxy]-2,4,6,8,10,12-hexamethyltridec-8-en-1-ol
• 化学式: C₄₁H₇₈O₇Si₂
• 分子量: 739.237
• InChiKey: ZKYIETPFDLCVFC-KBGILDMFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.49
• 重原子数：
  50
• 可旋转键数：
  24
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  75.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R,5R,6S,10S,11R,12S)-5,13-bis[[tert-butyl(dimethyl)silyl]oxy]-11-(methoxymethoxy)-3-[(4-methoxyphenyl)methoxy]-2,4,6,8,10,12-hexamethyltridec-8-en-1-ol 在 碳酸氢钠 、 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 生成
  参考文献：
  名称：

  A Practical Improvement, Enhancing the Large-Scale Synthesis of (+)-Discodermolide:  A Third-Generation Approach

  摘要：

  A significant improvement to the Penn one-gram synthesis of (+)-discodermolide (1) has been achieved. Specifically, reduction of the steric bulk of the C(11) hydroxyl protecting group permits formation of the requisite AB Wittig salt at the expense of the undesired intramolecular cyclization upon treatment with PPh3 at ambient pressure.

  DOI：

  10.1021/ol035697i
• 作为产物：
  描述：

  (2R,3S,4S)-3-hydroxy-5-(4-methoxybenzyloxy)-2,4-dimethylpentanoic acid methoxymethylamide 在 咪唑 、 水 、 叔丁基锂 、 二异丁基氢化铝 、 N,N-二异丙基乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 甲苯 、 正戊烷 为溶剂， 反应 31.17h， 生成 (2S,3S,4R,5R,6S,10S,11R,12S)-5,13-bis[[tert-butyl(dimethyl)silyl]oxy]-11-(methoxymethoxy)-3-[(4-methoxyphenyl)methoxy]-2,4,6,8,10,12-hexamethyltridec-8-en-1-ol
  参考文献：
  名称：

  A Practical Improvement, Enhancing the Large-Scale Synthesis of (+)-Discodermolide:  A Third-Generation Approach

  摘要：

  A significant improvement to the Penn one-gram synthesis of (+)-discodermolide (1) has been achieved. Specifically, reduction of the steric bulk of the C(11) hydroxyl protecting group permits formation of the requisite AB Wittig salt at the expense of the undesired intramolecular cyclization upon treatment with PPh3 at ambient pressure.

  DOI：

  10.1021/ol035697i

文献信息

• A Practical Improvement, Enhancing the Large-Scale Synthesis of (+)-Discodermolide:  A Third-Generation Approach
  作者：Amos B. Smith、B. Scott Freeze、Ignacio Brouard、Tomoyasu Hirose

  DOI：10.1021/ol035697i

  日期：2003.11.1

  A significant improvement to the Penn one-gram synthesis of (+)-discodermolide (1) has been achieved. Specifically, reduction of the steric bulk of the C(11) hydroxyl protecting group permits formation of the requisite AB Wittig salt at the expense of the undesired intramolecular cyclization upon treatment with PPh3 at ambient pressure.