(5S,10R,14S,15R,17S,18S,E)-5-allyl-10-(tert-butyldimethylsilyloxy)-3,3-diethyl-7-hydroxy-20,20-diisopropyl-15-(4-methoxybenzyloxy)-10,14,17,18,21-pentamethyl-4,19-dioxa-3,20-disiladocos-11-en-9-one | 1373432-46-2

• 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: (5S,10R,14S,15R,17S,18S,E)-5-allyl-10-(tert-butyldimethylsilyloxy)-3,3-diethyl-7-hydroxy-20,20-diisopropyl-15-(4-methoxybenzyloxy)-10,14,17,18,21-pentamethyl-4,19-dioxa-3,20-disiladocos-11-en-9-one
• CAS: 1373432-46-2
• 化学式: C₅₀H₉₄O₇Si₃
• 分子量: 891.549
• InChiKey: UBXSNHFNUSBBQX-MIRMTDNGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.23
• 重原子数：
  60.0
• 可旋转键数：
  30.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  83.45
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (5S,10R,14S,15R,17S,18S,E)-5-allyl-10-(tert-butyldimethylsilyloxy)-3,3-diethyl-7-hydroxy-20,20-diisopropyl-15-(4-methoxybenzyloxy)-10,14,17,18,21-pentamethyl-4,19-dioxa-3,20-disiladocos-11-en-9-one 在 三苯基膦氢溴酸盐 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以66%的产率得到(2S,6S)-6-allyl-2-((5R,9S,10R,12S,13S,E)-15,15-diisopropyl-10-(4-methoxybenzyloxy)-2,2,3,3,5,9,12,13,16-nonamethyl-4,14-dioxa-3,15-disilaheptadec-6-en-5-yl)-2-methoxytetrahydro-2H-pyran-4-ol
  参考文献：
  名称：

  Enantioselective Synthesis of the C1–C6 and C7–C23 Fragments of the Proposed Structure of Iriomoteolide 1a

  摘要：

  Synthesis of the C1-C6 and C7-C23 fragments of the proposed structure of Iriomoteolide 1a has been accomplished. Key steps include a cross metathesis to form the C15-C16 E olefin and a chelation controlled Grignard addition to form the tertiary alcohol at C14. Notably, 7 of the 9 stereocenters of the proposed structure have been set using various aldol reactions employing metallo enolates of thiazolidinethiones.

  DOI：

  10.1021/ol300785c
• 作为产物：
  描述：

  (S)-1-((S)-4-mesityl-2-thioxothiazolidin-3-yl)-3-(triethylsilyloxy)hex-5-en-1-one 在 二异丁基氢化铝 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 (5S,10R,14S,15R,17S,18S,E)-5-allyl-10-(tert-butyldimethylsilyloxy)-3,3-diethyl-7-hydroxy-20,20-diisopropyl-15-(4-methoxybenzyloxy)-10,14,17,18,21-pentamethyl-4,19-dioxa-3,20-disiladocos-11-en-9-one
  参考文献：
  名称：

  Enantioselective Synthesis of the C1–C6 and C7–C23 Fragments of the Proposed Structure of Iriomoteolide 1a

  摘要：

  Synthesis of the C1-C6 and C7-C23 fragments of the proposed structure of Iriomoteolide 1a has been accomplished. Key steps include a cross metathesis to form the C15-C16 E olefin and a chelation controlled Grignard addition to form the tertiary alcohol at C14. Notably, 7 of the 9 stereocenters of the proposed structure have been set using various aldol reactions employing metallo enolates of thiazolidinethiones.

  DOI：

  10.1021/ol300785c