(E,4R,5S,6S,7R,8S)-7-[tert-butyl(dimethyl)silyl]oxy-2,4,6,8-tetramethyl-5-trimethylsilyloxydec-2-enal | 343764-46-5

• 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: (E,4R,5S,6S,7R,8S)-7-[tert-butyl(dimethyl)silyl]oxy-2,4,6,8-tetramethyl-5-trimethylsilyloxydec-2-enal
• CAS: 343764-46-5
• 化学式: C₂₃H₄₈O₃Si₂
• 分子量: 428.803
• InChiKey: KJLWYGGTCNFCNQ-JWLRHSHHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.06
• 重原子数：
  28
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,6R)-2-[(1E,3Z,5R)-7-(benzenesulfonyl)-3-ethyl-5-methylhepta-1,3-dienyl]-6-methoxy-3,6-dihydro-2H-pyran 、 (E,4R,5S,6S,7R,8S)-7-[tert-butyl(dimethyl)silyl]oxy-2,4,6,8-tetramethyl-5-trimethylsilyloxydec-2-enal 在 正丁基锂 、 乙酸酐 、 dipotassium hydrogenphosphate 、 sodium amalgam 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.0h， 生成 、 tert-butyl-[(3S,4R,5S,6S,7R,8E,10E,13R,14Z,16E)-15-ethyl-17-[(2R,6R)-6-methoxy-3,6-dihydro-2H-pyran-2-yl]-3,5,7,9,13-pentamethyl-6-trimethylsilyloxyheptadeca-8,10,14,16-tetraen-4-yl]oxy-dimethylsilane
  参考文献：
  名称：

  Total Synthesis of (−)-Callystatin A

  摘要：

  [GRAPHICS]An effective total synthesis of (-)-callystatin A (1), member of the leptomycin family of antibiotics, has been achieved. The synthesis features Evans extended aldol methodology to construct the northern polypropionate subunit and two separate Julia olefinations to assemble the conjugated dienes. The total synthesis proceeded in 2.3% overall yield with the longest linear sequence of 15 steps.

  DOI：

  10.1021/ol0158922
• 作为产物：
  描述：

  (S)-2-甲基丁醛 在 2,6-二甲基吡啶 、 manganese(IV) oxide 、 四氯化钛 、 二异丁基氢化铝 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 0.75h， 生成 (E,4R,5S,6S,7R,8S)-7-[tert-butyl(dimethyl)silyl]oxy-2,4,6,8-tetramethyl-5-trimethylsilyloxydec-2-enal
  参考文献：
  名称：

  Total Synthesis of (−)-Callystatin A

  摘要：

  [GRAPHICS]An effective total synthesis of (-)-callystatin A (1), member of the leptomycin family of antibiotics, has been achieved. The synthesis features Evans extended aldol methodology to construct the northern polypropionate subunit and two separate Julia olefinations to assemble the conjugated dienes. The total synthesis proceeded in 2.3% overall yield with the longest linear sequence of 15 steps.

  DOI：

  10.1021/ol0158922

文献信息

• Total Synthesis of (−)-Callystatin A
  作者：Amos B. Smith、Benjamin M. Brandt

  DOI：10.1021/ol0158922

  日期：2001.5.1

  [GRAPHICS]An effective total synthesis of (-)-callystatin A (1), member of the leptomycin family of antibiotics, has been achieved. The synthesis features Evans extended aldol methodology to construct the northern polypropionate subunit and two separate Julia olefinations to assemble the conjugated dienes. The total synthesis proceeded in 2.3% overall yield with the longest linear sequence of 15 steps.