benzyl 2-[(2R,6S)-6-[(2R,4R,5S,8R)-4,8-dihydroxy-5-methyl-2-phenylmethoxyundec-10-enyl]oxan-2-yl]-2-methylpropanoate | 864498-73-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl 2-[(2R,6S)-6-[(2R,4R,5S,8R)-4,8-dihydroxy-5-methyl-2-phenylmethoxyundec-10-enyl]oxan-2-yl]-2-methylpropanoate
• CAS: 864498-73-7
• 化学式: C₃₅H₅₀O₆
• 分子量: 566.778
• InChiKey: NKOWZNWAWPSLPR-UAKSOMLXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  41
• 可旋转键数：
  18
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  85.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  benzyl 2-[(2R,6S)-6-[(2R,4R,5S,8R)-4,8-dihydroxy-5-methyl-2-phenylmethoxyundec-10-enyl]oxan-2-yl]-2-methylpropanoate 在 acetylacetonatodicarbonylrhodium(l) 、 4,6-二(二苯基膦)吩嗪 氢气 、 氯化铵 、 戴斯-马丁氧化剂 、 三乙胺 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 18.58h， 生成 2-[(2R,6S)-6-((2S,4R,5S,8S)-2-Benzyloxy-5-methyl-12-oxo-4,8-bis-triethylsilanyloxy-pentadec-14-enyl)-tetrahydro-pyran-2-yl]-2-methyl-propionic acid benzyl ester
  参考文献：
  名称：

  Efficient Asymmetric Synthesis of (+)-SCH 351448

  摘要：

  An efficient and stereocontrolled total synthesis of (+)-SCH 351448, a novel activator of low-density lipoprotein receptor promoter, has been achieved with a longest linear sequence of 21 steps. Key steps include applications of the recently developed asymmetric allyl- and crotylsilane reagents and a new protodesilylative version of the tandem silylformylation/allyisilylation reaction, which provides an efficient synthesis of 1,5-syn-diols.

  DOI：

  10.1021/ol0515006
• 作为产物：
  描述：

  benzyl 2-[(2R,6S)-6-[(2S,4R,5S)-4-bis(prop-2-enyl)silyloxy-5-methyl-2-phenylmethoxyhept-6-enyl]oxan-2-yl]-2-methylpropanoate 在 acetylacetonatodicarbonylrhodium(l) 四丁基氟化铵 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 22.0h， 生成 benzyl 2-[(2R,6S)-6-[(2R,4R,5S,8R)-4,8-dihydroxy-5-methyl-2-phenylmethoxyundec-10-enyl]oxan-2-yl]-2-methylpropanoate
  参考文献：
  名称：

  Efficient Asymmetric Synthesis of (+)-SCH 351448

  摘要：

  An efficient and stereocontrolled total synthesis of (+)-SCH 351448, a novel activator of low-density lipoprotein receptor promoter, has been achieved with a longest linear sequence of 21 steps. Key steps include applications of the recently developed asymmetric allyl- and crotylsilane reagents and a new protodesilylative version of the tandem silylformylation/allyisilylation reaction, which provides an efficient synthesis of 1,5-syn-diols.

  DOI：

  10.1021/ol0515006

文献信息

• Efficient Asymmetric Synthesis of (+)-SCH 351448
  作者：Sergei Bolshakov、James L. Leighton

  DOI：10.1021/ol0515006

  日期：2005.8.1

  An efficient and stereocontrolled total synthesis of (+)-SCH 351448, a novel activator of low-density lipoprotein receptor promoter, has been achieved with a longest linear sequence of 21 steps. Key steps include applications of the recently developed asymmetric allyl- and crotylsilane reagents and a new protodesilylative version of the tandem silylformylation/allyisilylation reaction, which provides an efficient synthesis of 1,5-syn-diols.