(2S,6R,7R,8R)-2-[(4S,5S,6S)-2,2-ditert-butyl-6-[(2S,3R)-3-hydroxyhex-5-en-2-yl]-5-methyl-1,3,2-dioxasilinan-4-yl]-7-methoxy-6,8-dimethyl-10-tri(propan-2-yl)silyloxydecan-5-one | 1026896-17-2

• 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,6R,7R,8R)-2-[(4S,5S,6S)-2,2-ditert-butyl-6-[(2S,3R)-3-hydroxyhex-5-en-2-yl]-5-methyl-1,3,2-dioxasilinan-4-yl]-7-methoxy-6,8-dimethyl-10-tri(propan-2-yl)silyloxydecan-5-one
• CAS: 1026896-17-2
• 化学式: C₄₀H₈₀O₆Si₂
• 分子量: 713.243
• InChiKey: GCMKVJSKCRJUHB-BRQQZENSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.88
• 重原子数：
  48
• 可旋转键数：
  21
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,6R,7R,8R)-2-[(4S,5S,6S)-2,2-ditert-butyl-6-[(2S,3R)-3-hydroxyhex-5-en-2-yl]-5-methyl-1,3,2-dioxasilinan-4-yl]-7-methoxy-6,8-dimethyl-10-tri(propan-2-yl)silyloxydecan-5-one 在 2,6-二叔丁基吡啶 、 二甲基硫 、 sodium carbonate 作用下， 以 氯仿 为溶剂， 反应 5.0h， 生成 (3R,4S)-4-[(4S,5S,6S)-2,2-ditert-butyl-6-[(2S,6R,7R,8R)-7-methoxy-6,8-dimethyl-5-oxo-10-tri(propan-2-yl)silyloxydecan-2-yl]-5-methyl-1,3,2-dioxasilinan-4-yl]-3-methoxypentanal
  参考文献：
  名称：

  Studies in marine macrolide synthesis: A stereocontrolled synthesis of a C17-C32 subunit of scytophycin C.

  摘要：

  The C-17-C32 subunit 8 of scytophycin C was prepared in 11 steps (19% yield, 83% ds) from (S)-12. Key features include the dipropionate aldol construction of the stereopentad 11, the Brown asymmetric crotylboration leading to 10, followed by their Ba(OH)2-induced, Horner-Emmons coupling to give 23, and the BF3.OEt2-promoted allylation, 25 --> 26.

  DOI：

  10.1016/s0040-4039(00)73994-3
• 作为产物：
  描述：

  三异丙基氯硅烷 在 palladium on activated charcoal 咪唑 、 barium dihydroxide 、 重铬酸吡啶 、 正丁基锂 、 草酰氯 、 三氟化硼乙醚 、 氢气 、 戴斯-马丁氧化剂 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.2h， 生成 (2S,6R,7R,8R)-2-[(4S,5S,6S)-2,2-ditert-butyl-6-[(2S,3R)-3-hydroxyhex-5-en-2-yl]-5-methyl-1,3,2-dioxasilinan-4-yl]-7-methoxy-6,8-dimethyl-10-tri(propan-2-yl)silyloxydecan-5-one
  参考文献：
  名称：

  Studies in marine macrolide synthesis: A stereocontrolled synthesis of a C17-C32 subunit of scytophycin C.

  摘要：

  The C-17-C32 subunit 8 of scytophycin C was prepared in 11 steps (19% yield, 83% ds) from (S)-12. Key features include the dipropionate aldol construction of the stereopentad 11, the Brown asymmetric crotylboration leading to 10, followed by their Ba(OH)2-induced, Horner-Emmons coupling to give 23, and the BF3.OEt2-promoted allylation, 25 --> 26.

  DOI：

  10.1016/s0040-4039(00)73994-3

文献信息

• Studies in marine macrolide synthesis: A stereocontrolled synthesis of a C17-C32 subunit of scytophycin C.
  作者：Ian Paterson、Yeung Kap-Sun

  DOI：10.1016/s0040-4039(00)73994-3

  日期：1993.8

  The C-17-C32 subunit 8 of scytophycin C was prepared in 11 steps (19% yield, 83% ds) from (S)-12. Key features include the dipropionate aldol construction of the stereopentad 11, the Brown asymmetric crotylboration leading to 10, followed by their Ba(OH)2-induced, Horner-Emmons coupling to give 23, and the BF3.OEt2-promoted allylation, 25 --> 26.