(E)-(4R,11R)-4-(tert-Butyl-diphenyl-silanyloxy)-11-(2-trimethylsilanyl-ethoxymethoxy)-dodec-2-enoic acid methyl ester

• 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: (E)-(4R,11R)-4-(tert-Butyl-diphenyl-silanyloxy)-11-(2-trimethylsilanyl-ethoxymethoxy)-dodec-2-enoic acid methyl ester
• 英文别名: methyl (E,4R,11R)-4-[tert-butyl(diphenyl)silyl]oxy-11-(2-trimethylsilylethoxymethoxy)dodec-2-enoate
• 化学式: C₃₅H₅₆O₅Si₂
• 分子量: 612.998
• InChiKey: FOHRSGATXMITEU-VURFXSBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.72
• 重原子数：
  42
• 可旋转键数：
  21
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 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：

  (E)-(4R,11R)-4-(tert-Butyl-diphenyl-silanyloxy)-11-(2-trimethylsilanyl-ethoxymethoxy)-dodec-2-enoic acid methyl ester 在 丁硫醇 、 potassium carbonate 、 magnesium bromide 作用下， 以79%的产率得到(E)-(4R,11R)-4-(tert-Butyl-diphenyl-silanyloxy)-11-hydroxy-dodec-2-enoic acid methyl ester
  参考文献：
  名称：

  1,8-Stereocontrol by 1,5-induction using an allylstannane followed by a 2,3-Wittig rearrangement: Diastereoselective total synthesis of (±)-epipatulolide C

  摘要：

  The relative configurations of 1,8-stereogenic centres can be controlled by coupling the tin(IV) chloride promoted reactions of aldehydes with 4-alkoxypent-2-enylstannanes, which proceed with excellent 1,5-induction, with a 2,3-Wittig rearrangement: this approach has been used to complete a diastereoselective synthesis of (+/-)-epipatulolide C 16. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02428-9
• 作为产物：
  描述：

  tert-butyl-diphenyl-[(E,3R,10R)-1-phenyl-10-(2-trimethylsilylethoxymethoxy)undec-1-en-3-yl]oxysilane 在 二甲基硫 、 臭氧 作用下， 生成 (E)-(4R,11R)-4-(tert-Butyl-diphenyl-silanyloxy)-11-(2-trimethylsilanyl-ethoxymethoxy)-dodec-2-enoic acid methyl ester
  参考文献：
  名称：

  1,8-Stereocontrol by 1,5-induction using an allylstannane followed by a 2,3-Wittig rearrangement: Diastereoselective total synthesis of (±)-epipatulolide C

  摘要：

  The relative configurations of 1,8-stereogenic centres can be controlled by coupling the tin(IV) chloride promoted reactions of aldehydes with 4-alkoxypent-2-enylstannanes, which proceed with excellent 1,5-induction, with a 2,3-Wittig rearrangement: this approach has been used to complete a diastereoselective synthesis of (+/-)-epipatulolide C 16. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02428-9

文献信息

• An approach to aliphatic 1,8-stereocontrol: diastereoselective syntheses of (±)-patulolide C and (±)-epipatulolide C
  作者：E. Kate Hoegenauer、Eric J. Thomas

  DOI：10.1039/c2ob25992c

  日期：——

  5-dien-3-ol 17 was prepared from the tin(IV) chloride promoted reaction of 4-(2-trimethylsilylethoxy)methoxypent-2-enyl(tributyl)stannane 16 with acrolein (1,5-syn : 1,5-anti = 96 : 4). An Ireland–Claisen rearrangement of the corresponding benzoyloxyacetate 21 with in situ esterification of the resulting acid using trimethylsilyldiazomethane gave methyl (4E,7Z)-2,9-anti-2-benzyloxy-9-(2-trimethylsilylethoxy)methoxydeca-4

  溴化锡（IV）促进7-羟基-7-苯基庚-2-基（三丁基）锡烷11与苯甲醛的反应，生成差向异构体1,8-二苯基辛-3-烯-1,8-二醇12和因此开发了用于脂肪族1,8-立体控制的间接方法，以完成（±）-patulolide C 1和（±）-epipatulolide C 40的非对映选择性合成。由（四）氯化锡促进的4-（2-三甲基甲硅烷基乙氧基）甲氧基戊的反应制备了（5 Z）-3,7- syn -7-（2-三甲基甲硅烷基乙氧基）甲氧基辛基-1,5-二烯-3-醇17 -2-丙烯基（三丁基）锡烷16与丙烯醛（1,5- syn  ：1,5-反= 96：4）。使用三甲基甲硅烷基重氮甲烷对得到的酸进行原位酯化，对相应的苯甲酰氧基乙酸21进行爱尔兰-克莱森重排，得到甲基（4 E，7 Z）-2,9-抗-2-苄氧基-9-（2-三甲基甲硅烷基乙氧基）甲氧基癸四，7-二烯酸酯22连同其2,9- 10-15％顺式差向异构体26中，2
• 1,8-Stereocontrol by 1,5-induction using an allylstannane followed by a 2,3-Wittig rearrangement: Diastereoselective total synthesis of (±)-epipatulolide C
  作者：E.Kate Dorling、Andrew P. Thomas、Eric J. Thomas

  DOI：10.1016/s0040-4039(98)02428-9

  日期：1999.1

  The relative configurations of 1,8-stereogenic centres can be controlled by coupling the tin(IV) chloride promoted reactions of aldehydes with 4-alkoxypent-2-enylstannanes, which proceed with excellent 1,5-induction, with a 2,3-Wittig rearrangement: this approach has been used to complete a diastereoselective synthesis of (+/-)-epipatulolide C 16. (C) 1998 Elsevier Science Ltd. All rights reserved.