(R,2E,4E,6E)-1-(5-((1s,4S)-4-(tert-butyldimethylsilyloxy)-1-hydroxycyclohexyl)-2,4-bis(methoxymethoxy)pyridin-3-yl)-8-(tert-butyldimethylsilyloxymethyl)deca-2,4,6-trien-1-one | 1501971-56-7

• 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: (R,2E,4E,6E)-1-(5-((1s,4S)-4-(tert-butyldimethylsilyloxy)-1-hydroxycyclohexyl)-2,4-bis(methoxymethoxy)pyridin-3-yl)-8-(tert-butyldimethylsilyloxymethyl)deca-2,4,6-trien-1-one
• CAS: 1501971-56-7
• 化学式: C₃₈H₆₅NO₈Si₂
• 分子量: 720.107
• InChiKey: YDMKHBKBQIWCNS-VVBNNICXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  49.0
• 可旋转键数：
  18.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  105.57
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (R,2E,4E,6E)-1-(5-((1s,4S)-4-(tert-butyldimethylsilyloxy)-1-hydroxycyclohexyl)-2,4-bis(methoxymethoxy)pyridin-3-yl)-8-(tert-butyldimethylsilyloxymethyl)deca-2,4,6-trien-1-one 在 对甲苯磺酸 作用下， 以 四氢呋喃 、 正己烷 、 水 为溶剂， 反应 12.0h， 以47%的产率得到torrubiellone B
  参考文献：
  名称：

  Directed Orthometalation and the Asymmetric Total Synthesis of N-Deoxymilitarinone A and Torrubiellone B

  摘要：

  A diverted total synthesis (DTS) approach to the total synthesis of pyridone alkaloids N-deoxymilitarinone A (8) and torrubiellone B (10) has been developed. The common intermediate 14 was first assembled by a dual directed orthometalation process using a methoxymethyl group as directed metalation group. Other crucial steps include the assembly of polyenes under aldol condensation for DTS using general and concise strategy and diastereoselective synthesis of the syn-dimethyl array by an Evans aldol reaction.

  DOI：

  10.1021/ol402820d
• 作为产物：
  描述：

  (R)-2-((tert-butyldimethylsilyloxy)methyl)butan-1-ol 在 草酰氯 、 sodium hydride 、 二异丁基氢化铝 、 二甲基亚砜 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 (R,2E,4E,6E)-1-(5-((1s,4S)-4-(tert-butyldimethylsilyloxy)-1-hydroxycyclohexyl)-2,4-bis(methoxymethoxy)pyridin-3-yl)-8-(tert-butyldimethylsilyloxymethyl)deca-2,4,6-trien-1-one 、 (R,2Z,4E,6E)-1-(5-((1s,4S)-4-(tert-butyldimethylsilyloxy)-1-hydroxycyclohexyl)-2,4-bis(methoxymethoxy)pyridin-3-yl)-8-(tert-butyldimethylsilyloxymethyl)deca-2,4,6-trien-1-one
  参考文献：
  名称：

  Directed Orthometalation and the Asymmetric Total Synthesis of N-Deoxymilitarinone A and Torrubiellone B

  摘要：

  A diverted total synthesis (DTS) approach to the total synthesis of pyridone alkaloids N-deoxymilitarinone A (8) and torrubiellone B (10) has been developed. The common intermediate 14 was first assembled by a dual directed orthometalation process using a methoxymethyl group as directed metalation group. Other crucial steps include the assembly of polyenes under aldol condensation for DTS using general and concise strategy and diastereoselective synthesis of the syn-dimethyl array by an Evans aldol reaction.

  DOI：

  10.1021/ol402820d