(6E,8Z,10S,11R,12E,14S,15R)-11-hydroxy-10,12,14-trimethyl-2-phenylseleno-15-(triethylsilyl)oxy-6,8,12-hexadecatrienoic acid | 1440534-65-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (6E,8Z,10S,11R,12E,14S,15R)-11-hydroxy-10,12,14-trimethyl-2-phenylseleno-15-(triethylsilyl)oxy-6,8,12-hexadecatrienoic acid
• 英文别名: (6E,8Z,10S,11R,12E,14S,15R)-11-hydroxy-10,12,14-trimethyl-2-phenylselanyl-15-triethylsilyloxyhexadeca-6,8,12-trienoic acid
• CAS: 1440534-65-5
• 化学式: C₃₁H₅₀O₄SeSi
• 分子量: 593.781
• InChiKey: LELGJPIADCULFT-AYRPAHKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.16
• 重原子数：
  37
• 可旋转键数：
  18
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (6E,8Z,10S,11R,12E,14S,15R)-11-hydroxy-10,12,14-trimethyl-2-phenylseleno-15-(triethylsilyl)oxy-6,8,12-hexadecatrienoic acid 在 sodium periodate 、 2,4,6-三氯苯甲酰氯 、 三乙胺 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 14.5h， 生成 (3E,7E,9Z,11S,12R)-12-((4S,5R,E)-5-hydroxy-4-methylhex-2-en-2-yl)-11-methyloxacyclodo-deca-3,7,9-trien-2-one
  参考文献：
  名称：

  Formal Total Synthesis of Lactimidomycin

  摘要：

  A concise synthesis of an intermediate of lactimidomycin, a glutarimide-containing macrocyclic polyketide produced by an actinomycete, has been accomplished in 35% overall yield from a known vinylketene silyl N,O-acetal by a 10-step sequence that involves two types of asymmetric aldol reactions to install all the stereocenters, the Stille coupling to set up the whole carbon famework, and the Yamaguchi lactonization to construct the 12-membered macrolactone ring.

  DOI：

  10.1021/ol401214f
• 作为产物：
  描述：

  (S)-4-benzyl-3-((2E,4S,5R)-5-hydroxy-2,4-dimethyl-2-hexenoyl)-2-oxazolidinone 在 咪唑 、 三乙基硅烷 、 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 tin(II) trifluoromethanesulfonate 、 lithium hydroxide monohydrate 、 (R)-1-methyl-2-(1-naphthylaminomethyl)pyrrolidine 、 palladium 10% on activated carbon 、 sodium hexamethyldisilazane 、 二异丁基氢化铝 、 copper(l) chloride 、 lithium chloride 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 127.34h， 生成 (6E,8Z,10S,11R,12E,14S,15R)-11-hydroxy-10,12,14-trimethyl-2-phenylseleno-15-(triethylsilyl)oxy-6,8,12-hexadecatrienoic acid
  参考文献：
  名称：

  Formal Total Synthesis of Lactimidomycin

  摘要：

  A concise synthesis of an intermediate of lactimidomycin, a glutarimide-containing macrocyclic polyketide produced by an actinomycete, has been accomplished in 35% overall yield from a known vinylketene silyl N,O-acetal by a 10-step sequence that involves two types of asymmetric aldol reactions to install all the stereocenters, the Stille coupling to set up the whole carbon famework, and the Yamaguchi lactonization to construct the 12-membered macrolactone ring.

  DOI：

  10.1021/ol401214f

文献信息

• Formal Total Synthesis of Lactimidomycin
  作者：Tomohiro Nagasawa、Shigefumi Kuwahara

  DOI：10.1021/ol401214f

  日期：2013.6.21

  A concise synthesis of an intermediate of lactimidomycin, a glutarimide-containing macrocyclic polyketide produced by an actinomycete, has been accomplished in 35% overall yield from a known vinylketene silyl N,O-acetal by a 10-step sequence that involves two types of asymmetric aldol reactions to install all the stereocenters, the Stille coupling to set up the whole carbon famework, and the Yamaguchi lactonization to construct the 12-membered macrolactone ring.