(4S,5R)-4-(N,N-dibenzylamino)-1-(tert-butyldimethylsilyloxy)-5-heptadecanol | 366785-11-7

• 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: (4S,5R)-4-(N,N-dibenzylamino)-1-(tert-butyldimethylsilyloxy)-5-heptadecanol
• 英文别名: (4S,5R)-1-[tert-butyl(dimethyl)silyl]oxy-4-(dibenzylamino)heptadecan-5-ol
• CAS: 366785-11-7
• 化学式: C₃₇H₆₃NO₂Si
• 分子量: 581.998
• InChiKey: LKQGKUOHCKGWSC-MPQUPPDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.53
• 重原子数：
  41
• 可旋转键数：
  23
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  32.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4S,5R)-4-(N,N-dibenzylamino)-1-(tert-butyldimethylsilyloxy)-5-heptadecanol 在 palladium dihydroxide 氢气 作用下， 以 甲醇 为溶剂， 反应 3.5h， 生成 (4S,5R)-4-Amino-1-(tert-butyl-dimethyl-silanyloxy)-heptadecan-5-ol
  参考文献：
  名称：

  Stereoselective synthesis of (5S,6S)- and (5S,6R)-aza-muricatacin from an l-glutamic acid derivative

  摘要：

  A stereodivergent synthesis of threo and erythro aza-muricatacin. a non-natural aza-analogue of the bioactive annonaceous acetogenin muricatacin, is presented. The configuration of the C(5) stereocenter is controlled by diastereoselective alkylation of alpha -dibenzylamino aldehyde I or diastercoselective reduction of alpha -dibenzylamino ketone 3. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00251-8
• 作为产物：
  描述：

  magnesium,dodecane,bromide 、 (-)-S-5-(tert-butyldimethylsilyloxy)-2-(N,N-dibenzylamino)-1-pentanal 以 乙醚 为溶剂， 反应 1.5h， 以70%的产率得到(4S,5R)-4-(N,N-dibenzylamino)-1-(tert-butyldimethylsilyloxy)-5-heptadecanol
  参考文献：
  名称：

  Stereoselective synthesis of (5S,6S)- and (5S,6R)-aza-muricatacin from an l-glutamic acid derivative

  摘要：

  A stereodivergent synthesis of threo and erythro aza-muricatacin. a non-natural aza-analogue of the bioactive annonaceous acetogenin muricatacin, is presented. The configuration of the C(5) stereocenter is controlled by diastereoselective alkylation of alpha -dibenzylamino aldehyde I or diastercoselective reduction of alpha -dibenzylamino ketone 3. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00251-8

文献信息

• Stereoselective synthesis of (5S,6S)- and (5S,6R)-aza-muricatacin from an l-glutamic acid derivative
  作者：José M. Andrés、Noemı́ de Elena、Rafael Pedrosa、Alfonso Pérez-Encabo

  DOI：10.1016/s0957-4166(01)00251-8

  日期：2001.6

  A stereodivergent synthesis of threo and erythro aza-muricatacin. a non-natural aza-analogue of the bioactive annonaceous acetogenin muricatacin, is presented. The configuration of the C(5) stereocenter is controlled by diastereoselective alkylation of alpha -dibenzylamino aldehyde I or diastercoselective reduction of alpha -dibenzylamino ketone 3. (C) 2001 Elsevier Science Ltd. All rights reserved.