(3R,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-4-(tert-butyl-dimethyl-silanyloxymethyl)-hex-5-enoic acid methyl ester | 276879-11-9

• 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: (3R,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-4-(tert-butyl-dimethyl-silanyloxymethyl)-hex-5-enoic acid methyl ester
• 英文别名: methyl (3R,4S)-3-[tert-butyl(dimethyl)silyl]oxy-4-[[tert-butyl(dimethyl)silyl]oxymethyl]hex-5-enoate
• CAS: 276879-11-9
• 化学式: C₂₀H₄₂O₄Si₂
• 分子量: 402.722
• InChiKey: DSLOJUBZIYNNMS-DLBZAZTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.76
• 重原子数：
  26
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3R,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-4-(tert-butyl-dimethyl-silanyloxymethyl)-hex-5-enoic acid methyl ester 在 titanium(IV) isopropylate 、 异丙基氯化镁 、 吡啶 、 三氯化铁 、 sodium acetate 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 、 甲醇 为溶剂， 以72%的产率得到(4R,5S)-4-tert-butyldimethylsilyloxymethyl-5-tert-butyldimethylsilyloxycyclohex-2-en-1-one
  参考文献：
  名称：

  Optically active trans-4-(tert-butyldimethylsiloxymethyl)-5-(tert-butyldimethylsiloxy)-2-cyclohexenone as a useful chiral building block for preparation of substituted cyclohexane rings: synthesis and its highly stereoselective reaction with RCu(CN)Li

  摘要：

  Optically active trans-4-(tert-butyldimethylsiloxymethyl)-5-(tert-butyldimethylsiloxy)-2cyclohexenone (2) has been synthesized in 25% overall yield starting from easily available 1,4-bis(benzyloxy)-2,3-epoxy butane (3). The enone 2 reacts with excellent stereoselectivity with RCu(CN)Li thus working as an efficient chiral building block for preparation of substituted cyclohexane compounds. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00239-2
• 作为产物：
  描述：

  tert-Butyl-dimethyl-((S)-(S)-2-oxiranyl-but-3-enyloxy)-silane 在 咪唑 、 sodium chlorite 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 、 二异丁基氢化铝 、 potassium carbonate 作用下， 以 四氢呋喃 、 正己烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 、 叔丁醇 为溶剂， 反应 2.0h， 生成 (3R,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-4-(tert-butyl-dimethyl-silanyloxymethyl)-hex-5-enoic acid methyl ester
  参考文献：
  名称：

  Optically active trans-4-(tert-butyldimethylsiloxymethyl)-5-(tert-butyldimethylsiloxy)-2-cyclohexenone as a useful chiral building block for preparation of substituted cyclohexane rings: synthesis and its highly stereoselective reaction with RCu(CN)Li

  摘要：

  Optically active trans-4-(tert-butyldimethylsiloxymethyl)-5-(tert-butyldimethylsiloxy)-2cyclohexenone (2) has been synthesized in 25% overall yield starting from easily available 1,4-bis(benzyloxy)-2,3-epoxy butane (3). The enone 2 reacts with excellent stereoselectivity with RCu(CN)Li thus working as an efficient chiral building block for preparation of substituted cyclohexane compounds. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00239-2

文献信息

• Optically active trans-4-(tert-butyldimethylsiloxymethyl)-5-(tert-butyldimethylsiloxy)-2-cyclohexenone as a useful chiral building block for preparation of substituted cyclohexane rings: synthesis and its highly stereoselective reaction with RCu(CN)Li
  作者：Takeshi Hanazawa、Masakazu Koiwa、Georges P.-J. Hareau、Fumie Sato

  DOI：10.1016/s0040-4039(00)00239-2

  日期：2000.4

  Optically active trans-4-(tert-butyldimethylsiloxymethyl)-5-(tert-butyldimethylsiloxy)-2cyclohexenone (2) has been synthesized in 25% overall yield starting from easily available 1,4-bis(benzyloxy)-2,3-epoxy butane (3). The enone 2 reacts with excellent stereoselectivity with RCu(CN)Li thus working as an efficient chiral building block for preparation of substituted cyclohexane compounds. (C) 2000 Elsevier Science Ltd. All rights reserved.