(R)-2-{(4S,5R,6S)-6-[(1S,4S,5R,6S,7S,8R)-8-Benzyloxymethoxy-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-1,5,7-trimethyl-3-oxo-nonyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-propionic acid | 141566-35-0

• 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: (R)-2-{(4S,5R,6S)-6-[(1S,4S,5R,6S,7S,8R)-8-Benzyloxymethoxy-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-1,5,7-trimethyl-3-oxo-nonyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-propionic acid
• 英文别名: (2R)-2-[(4S,5R,6S)-6-[(2S,5S,6R,7S,8S,9R)-5,7-bis[[tert-butyl(dimethyl)silyl]oxy]-6,8-dimethyl-4-oxo-9-(phenylmethoxymethoxy)decan-2-yl]-2,2,5-trimethyl-1,3-dioxan-4-yl]propanoic acid
• CAS: 141566-35-0
• 化学式: C₄₂H₇₆O₉Si₂
• 分子量: 781.231
• InChiKey: KVIBXDWFWOQKMY-JUDZXSOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.09
• 重原子数：
  53.0
• 可旋转键数：
  19.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  109.75
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (R)-2-{(4S,5R,6S)-6-[(1S,4S,5R,6S,7S,8R)-8-Benzyloxymethoxy-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-1,5,7-trimethyl-3-oxo-nonyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-propionic acid 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 (2R,3S,4R,5S,6S,9S,10R,11S,12S,13R)-9,11-bis(tert-butyldimethylsiloxy)-13-hydroxy-3,5-(isopropylidenedioxy)-2,4,6,10,12-pentamethyl-8-oxotetradecanoic acid
  参考文献：
  名称：

  Studies in macrolide synthesis: A stereocontrolled synthesis of a (9S)-macrolide intermediate for oleandomycin using chiral boron reagents.

  摘要：

  The (9S)-macrolide 1 (P = TBS) was prepared in 14 steps (5% yield) with 63% overall ds starting from the ethyl ketone (S)-2. The C1-C7 and C8-C13 segments, 3 and 4, were obtained via boron enolate aldol reactions mediated by (+)- and (-)-(Ipc)2BOTf, respectively.

  DOI：

  10.1016/s0040-4039(00)91728-3
• 作为产物：
  描述：

  (2S,3S,4S,5R,6S)-7-hydroxy-3,5-(isopropylidenedioxy)-2,4,6-trimethylheptyl p-toluenesulfonate 在 W-2 Ra Ni potassium permanganate 、 sodium periodate 、 草酰氯 、 氢气 、 二甲基亚砜 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇二甲醚 、 乙醚 、 水 、 叔丁醇 为溶剂， 反应 27.5h， 生成 (R)-2-{(4S,5R,6S)-6-[(1S,4S,5R,6S,7S,8R)-8-Benzyloxymethoxy-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-1,5,7-trimethyl-3-oxo-nonyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-propionic acid
  参考文献：
  名称：

  Studies in macrolide synthesis: A stereocontrolled synthesis of a (9S)-macrolide intermediate for oleandomycin using chiral boron reagents.

  摘要：

  The (9S)-macrolide 1 (P = TBS) was prepared in 14 steps (5% yield) with 63% overall ds starting from the ethyl ketone (S)-2. The C1-C7 and C8-C13 segments, 3 and 4, were obtained via boron enolate aldol reactions mediated by (+)- and (-)-(Ipc)2BOTf, respectively.

  DOI：

  10.1016/s0040-4039(00)91728-3