(S)-benzyl 1-(tert-butyldimethylsilyloxy)-4-oxobutan-2-ylcarbamate | 1352964-64-7

• 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: (S)-benzyl 1-(tert-butyldimethylsilyloxy)-4-oxobutan-2-ylcarbamate
• 英文别名: (S)-3-(Cbz-amino)-4-(tert-butyldimethylsilyloxy)butanal；benzyl N-[(2S)-1-[tert-butyl(dimethyl)silyl]oxy-4-oxobutan-2-yl]carbamate
• CAS: 1352964-64-7
• 化学式: C₁₈H₂₉NO₄Si
• 分子量: 351.518
• InChiKey: IDHMDZKLRSHDET-INIZCTEOSA-N

物化性质

• 沸点：
  447.9±45.0 °C(Predicted)
• 密度：
  1.035±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.89
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-benzyl 1-(tert-butyldimethylsilyloxy)-4-oxobutan-2-ylcarbamate 在 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 29.0h， 生成 (2S,6S)-1-benzyl-2-((tert-butyldimethylsilyloxy)methyl)-6-methylpiperidine
  参考文献：
  名称：

  Synthesis of (−)-dihydropinidine, (2S,6R)-isosolenopsin and (+)-monomorine via a chiral synthon from l-aspartic acid

  摘要：

  The use of beta-amino aldehyde derived from L-aspartic acid as a chiral synthon to construct 2,6-disubstituted piperidines is described. The synthesis of (-)-dihydropinidine center dot HCl, (2S,6R)-isosolenopsin center dot HCl and (+)-monomorine has been achieved from this chiral synthon using a Wittig reaction followed by hydrogenation (reductive cyclization) as the key steps. CD (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.11.006
• 作为产物：
  描述：

  N-(benzyloxycarbonyl)-L-aspartic acid 4-methyl ester 在 N-甲基吗啉 、 咪唑 、 氯甲酸乙酯 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 15.92h， 生成 (S)-benzyl 1-(tert-butyldimethylsilyloxy)-4-oxobutan-2-ylcarbamate
  参考文献：
  名称：

  Synthesis of (−)-dihydropinidine, (2S,6R)-isosolenopsin and (+)-monomorine via a chiral synthon from l-aspartic acid

  摘要：

  The use of beta-amino aldehyde derived from L-aspartic acid as a chiral synthon to construct 2,6-disubstituted piperidines is described. The synthesis of (-)-dihydropinidine center dot HCl, (2S,6R)-isosolenopsin center dot HCl and (+)-monomorine has been achieved from this chiral synthon using a Wittig reaction followed by hydrogenation (reductive cyclization) as the key steps. CD (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.11.006

文献信息

• Enantioselective access to (−)-indolizidines 167B, 209D, 239AB, 195B and (−)-monomorine from a common chiral synthon
  作者：Chada Raji Reddy、Bellamkonda Latha、Nagavaram Narsimha Rao

  DOI：10.1016/j.tet.2011.10.076

  日期：2012.1

  An enantioselective access to (−)-indolizidine alkaloids 167B, 209D, 239AB, 195B and (−)-monomorine from a new chiral synthon is described. The use of (S)-3-(Cbz-amino)-4-(tert-butyldimethylsilyloxy)butanal, obtained from l-aspartic acid, has provided efficient access of the indolizidine frame work through a Horner–Wadsworth–Emmons reaction and reductive cyclization as the key steps.

  描述了从新的手性合成子对（-）-吲哚并立定生物碱167B，209D，239AB，195B和（-）-单morine的对映选择性访问。从l-天冬氨酸获得的（S）-3-（Cbz-氨基）-4-（叔丁基二甲基甲硅烷氧基）丁醛的使用通过Horner-Wadsworth-Emmons反应和还原反应提供了吲哚并立定骨架的有效通道环化是关键步骤。
• Synthesis of (−)-dihydropinidine, (2S,6R)-isosolenopsin and (+)-monomorine via a chiral synthon from l-aspartic acid
  作者：Chada Raji Reddy、Bellamkonda Latha

  DOI：10.1016/j.tetasy.2011.11.006

  日期：2011.11

  The use of beta-amino aldehyde derived from L-aspartic acid as a chiral synthon to construct 2,6-disubstituted piperidines is described. The synthesis of (-)-dihydropinidine center dot HCl, (2S,6R)-isosolenopsin center dot HCl and (+)-monomorine has been achieved from this chiral synthon using a Wittig reaction followed by hydrogenation (reductive cyclization) as the key steps. CD (C) 2011 Elsevier Ltd. All rights reserved.