(1S,5S,6Z,9Z,13S,15S)-5-(t-butyldimethylsilyloxy)-10-chloro-15-[(triphenylmethoxy)methyl]-6-methyl-2,14-dioxabicyclo[11.2.1]hexadeca-6,9-dien-3-one | 629614-55-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (1S,5S,6Z,9Z,13S,15S)-5-(t-butyldimethylsilyloxy)-10-chloro-15-[(triphenylmethoxy)methyl]-6-methyl-2,14-dioxabicyclo[11.2.1]hexadeca-6,9-dien-3-one
• 英文别名: (1S,5S,6Z,9Z,13S,15S)-5-[tert-butyl(dimethyl)silyl]oxy-10-chloro-6-methyl-15-(trityloxymethyl)-2,14-dioxabicyclo[11.2.1]hexadeca-6,9-dien-3-one
• CAS: 629614-55-7
• 化学式: C₄₁H₅₁ClO₅Si
• 分子量: 687.391
• InChiKey: BKFALMAIQHXPOB-NIBLYXTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.1
• 重原子数：
  48
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1S,5S,6Z,9Z,13S,15S)-5-(t-butyldimethylsilyloxy)-10-chloro-15-[(triphenylmethoxy)methyl]-6-methyl-2,14-dioxabicyclo[11.2.1]hexadeca-6,9-dien-3-one 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以85%的产率得到(1S,5S,6Z,9Z,13S,15S)-10-chloro-5-hydroxy-15-[(triphenylmethoxy)methyl]-6-methyl-2,14-dioxabicyclo[11.2.1]hexadeca-6,9-dien-3-one
  参考文献：
  名称：

  Synthesis of ent-Haterumalide NA (ent-Oocydin A) Methyl Ester

  摘要：

  Stille coupling of allylic chloride 26 with vinylstannane 4a afforded 65% of 27 with the requisite skipped diene, vinyl chloride, and allylic oxygen functionality. Yamaguchi macrolactonization of 28 provided 65% of 29, which was elaborated to haterumalide NA methyl ester (32) by a Nozaki-Hiyama-Kishi coupling with 31.

  DOI：

  10.1021/ol0356789
• 作为产物：
  描述：

  phenyl (3S,4Z,7Z)-3-(t-butyldimethylsilyloxy)-8-chloro-4-methyl-10-[(2S,4S,5S)-tetrahydro-4-hydroxy-5-(triphenylmethoxymethyl)-2-furanyl]-4,7-decadienoate 在 4-二甲氨基吡啶 、 氢氧化钾 、 水 、 三乙胺 作用下， 以 四氢呋喃 、 甲苯 、 叔丁醇 为溶剂， 反应 25.0h， 生成 (1S,5S,6Z,9Z,13S,15S)-5-(t-butyldimethylsilyloxy)-10-chloro-15-[(triphenylmethoxy)methyl]-6-methyl-2,14-dioxabicyclo[11.2.1]hexadeca-6,9-dien-3-one
  参考文献：
  名称：

  Synthesis of ent-Haterumalide NA (ent-Oocydin A) Methyl Ester

  摘要：

  Stille coupling of allylic chloride 26 with vinylstannane 4a afforded 65% of 27 with the requisite skipped diene, vinyl chloride, and allylic oxygen functionality. Yamaguchi macrolactonization of 28 provided 65% of 29, which was elaborated to haterumalide NA methyl ester (32) by a Nozaki-Hiyama-Kishi coupling with 31.

  DOI：

  10.1021/ol0356789

文献信息

• Synthesis of <i>ent</i>-Haterumalide NA (<i>ent</i>-Oocydin A) Methyl Ester
  作者：Yonghong Gu、Barry B. Snider

  DOI：10.1021/ol0356789

  日期：2003.11.1

  Stille coupling of allylic chloride 26 with vinylstannane 4a afforded 65% of 27 with the requisite skipped diene, vinyl chloride, and allylic oxygen functionality. Yamaguchi macrolactonization of 28 provided 65% of 29, which was elaborated to haterumalide NA methyl ester (32) by a Nozaki-Hiyama-Kishi coupling with 31.