(E)-(2R,3S,4S,6R,7R,10S)-2,7-Bis-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-4,6,8,10-tetramethyl-5,11-dioxo-dodec-8-enoic acid tert-butyl ester | 903558-86-1

• 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)-(2R,3S,4S,6R,7R,10S)-2,7-Bis-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-4,6,8,10-tetramethyl-5,11-dioxo-dodec-8-enoic acid tert-butyl ester
• 英文别名: tert-butyl (E,2R,3S,4S,6R,7R,10S)-2,7-bis[[tert-butyl(dimethyl)silyl]oxy]-3-methoxy-4,6,8,10-tetramethyl-5,11-dioxododec-8-enoate
• CAS: 903558-86-1
• 化学式: C₃₃H₆₄O₇Si₂
• 分子量: 629.038
• InChiKey: UTZAYQXAWSBKFT-CLPFKIKQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.14
• 重原子数：
  42
• 可旋转键数：
  18
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (E)-(2R,3S,4S,6R,7R,10S)-2,7-Bis-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-4,6,8,10-tetramethyl-5,11-dioxo-dodec-8-enoic acid tert-butyl ester 、 (6E,9Z)-(2S,3R,4S,5S,8S)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-3-(4-methoxy-benzyloxy)-2,6,8-trimethyl-5-triethylsilanyloxy-undeca-6,9-dienal 在 (+)-β-chlorodiisopinocampheylborane 、 三乙胺 作用下， 以 乙醚 为溶剂， 反应 1.0h， 生成 tert-butyl (2R,3S,4S,6R,7R,8E,10S,13R,14R,15S,16S,17S,18E,20S,21Z)-2,7-bis[[tert-butyl(dimethyl)silyl]oxy]-16-[[tert-butyl(dimethyl)silyl]oxymethyl]-13-hydroxy-3-methoxy-15-[(4-methoxyphenyl)methoxy]-4,6,8,10,14,18,20-heptamethyl-5,11-dioxo-17-triethylsilyloxytricosa-8,18,21-trienoate 、 tert-butyl (2R,3S,4S,6R,7R,8E,10S,13S,14R,15S,16S,17S,18E,20S,21Z)-2,7-bis[[tert-butyl(dimethyl)silyl]oxy]-16-[[tert-butyl(dimethyl)silyl]oxymethyl]-13-hydroxy-3-methoxy-15-[(4-methoxyphenyl)methoxy]-4,6,8,10,14,18,20-heptamethyl-5,11-dioxo-17-triethylsilyloxytricosa-8,18,21-trienoate
  参考文献：
  名称：

  Synthetic studies toward the total synthesis of tedanolide: assembly of the C1–C23 carbon backbone

  摘要：

  A stereoselective assembly of the C1-C23 fragment representing the carbon backbone of tedanolide was accomplished utilizing a chiral boron reagent to effect the aldol coupling of the C1-C12 diketoester fragment with the C13-C23 aldehyde fragment. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.04.044
• 作为产物：
  描述：

  tert-Butyl-[(S)-3-(4-methoxy-benzyloxy)-2-methyl-butoxy]-diphenyl-silane 在 吡啶 、 2,6-二甲基吡啶 、 三氟甲磺酸二丁硼 、 四丁基氟化铵 、 二异丁基氢化铝 、 戴斯-马丁氧化剂 、 三乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (E)-(2R,3S,4S,6R,7R,10S)-2,7-Bis-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-4,6,8,10-tetramethyl-5,11-dioxo-dodec-8-enoic acid tert-butyl ester
  参考文献：
  名称：

  Synthetic studies toward the total synthesis of tedanolide: assembly of the C1–C23 carbon backbone

  摘要：

  A stereoselective assembly of the C1-C23 fragment representing the carbon backbone of tedanolide was accomplished utilizing a chiral boron reagent to effect the aldol coupling of the C1-C12 diketoester fragment with the C13-C23 aldehyde fragment. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.04.044

文献信息

• Synthetic studies toward the total synthesis of tedanolide: assembly of the C1–C23 carbon backbone
  作者：Chek-Ming Wong、Teck-Peng Loh

  DOI：10.1016/j.tetlet.2006.04.044

  日期：2006.6

  A stereoselective assembly of the C1-C23 fragment representing the carbon backbone of tedanolide was accomplished utilizing a chiral boron reagent to effect the aldol coupling of the C1-C12 diketoester fragment with the C13-C23 aldehyde fragment. (c) 2006 Elsevier Ltd. All rights reserved.