(2S,3S,4S,5S,E)-5-(tert-butyldimethylsilyloxy)-2,4-dimethyl-7-phenylhept-6-ene-1,3-diol | 387822-03-9

• 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: (2S,3S,4S,5S,E)-5-(tert-butyldimethylsilyloxy)-2,4-dimethyl-7-phenylhept-6-ene-1,3-diol
• 英文别名: (E,2S,3S,4S,5S)-5-[tert-butyl(dimethyl)silyl]oxy-2,4-dimethyl-7-phenylhept-6-ene-1,3-diol
• CAS: 387822-03-9
• 化学式: C₂₁H₃₆O₃Si
• 分子量: 364.601
• InChiKey: VJHXCHOFQUQGIT-SMNKCIGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.72
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,3S,4S,5S,E)-5-(tert-butyldimethylsilyloxy)-2,4-dimethyl-7-phenylhept-6-ene-1,3-diol 在 咪唑 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 17.0h， 生成 (3S,4R,5S,6S,E)-7-(tert-butyldiphenylsilyloxy)-4,6-dimethyl-1-phenylhept-1-ene-3,5-diol
  参考文献：
  名称：

  Total Synthesis of (+)-Crocacin D

  摘要：

  The total synthesis of (+)-crocacin D is described. The convergent asymmetric synthesis relies on the use of a Stille cross-coupling between an (E)-vinyl stannane with an (E)-vinyl iodide to establish the (E,E)-dienamide moiety followed by a mild and efficient copper-catalyzed coupling between (+)-crocacin C and a (Z)-vinyl iodide to establish the challenging (Z)-enamide function.

  DOI：

  10.1021/jo047732k
• 作为产物：
  描述：

  (2E,4S,5S,6E)-methyl 5-(tert-butyldimethylsilyloxy)-4-methyl-7-phenylhepta-2,6-dienoate 在 二异丁基氢化铝 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 23.0h， 生成 (2S,3S,4S,5S,E)-5-(tert-butyldimethylsilyloxy)-2,4-dimethyl-7-phenylhept-6-ene-1,3-diol
  参考文献：
  名称：

  Total Synthesis of (+)-Crocacin D

  摘要：

  The total synthesis of (+)-crocacin D is described. The convergent asymmetric synthesis relies on the use of a Stille cross-coupling between an (E)-vinyl stannane with an (E)-vinyl iodide to establish the (E,E)-dienamide moiety followed by a mild and efficient copper-catalyzed coupling between (+)-crocacin C and a (Z)-vinyl iodide to establish the challenging (Z)-enamide function.

  DOI：

  10.1021/jo047732k

文献信息

• Total Synthesis of (+)-Crocacin C
  作者：Luiz C. Dias、Luciana G. de Oliveira

  DOI：10.1021/ol016845c

  日期：2001.11.1

  [GRAPHICS]The total synthesis of (+)-crocacin C is described. The convergent asymmetric synthesis relies on the use of a regio- and diastereoselective epoxidation of an allylic alcohol with m-CPBA followed by epoxide opening with Me2CuCNLi2 and a Stille cross-coupling between E-vinyl stannane 5 and E-vinyl iodide 6 to establish the (E,E)-dienamide moiety.
• Total Synthesis of (+)-Crocacin D
  作者：Luiz C. Dias、Luciana G. de Oliveira、Janaína D. Vilcachagua、Florian Nigsch

  DOI：10.1021/jo047732k

  日期：2005.3.1

  The total synthesis of (+)-crocacin D is described. The convergent asymmetric synthesis relies on the use of a Stille cross-coupling between an (E)-vinyl stannane with an (E)-vinyl iodide to establish the (E,E)-dienamide moiety followed by a mild and efficient copper-catalyzed coupling between (+)-crocacin C and a (Z)-vinyl iodide to establish the challenging (Z)-enamide function.