(2S,1'S,2'S)-N-(tert-butoxycarbonyl)-2-(1'-hydroxy-2'-methyl-3'-butenyl)-pyrrolidine | 159248-94-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (2S,1'S,2'S)-N-(tert-butoxycarbonyl)-2-(1'-hydroxy-2'-methyl-3'-butenyl)-pyrrolidine
• 英文别名: tert-butyl (2S)-2-[(1S,2S)-1-hydroxy-2-methylbut-3-enyl]pyrrolidine-1-carboxylate
• CAS: 159248-94-9
• 化学式: C₁₄H₂₅NO₃
• 分子量: 255.357
• InChiKey: FAZLEVGCLGUJHN-SRVKXCTJSA-N

物化性质

• 沸点：
  347.2±15.0 °C(Predicted)
• 密度：
  1.041±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,1'S,2'S)-N-(tert-butoxycarbonyl)-2-(1'-hydroxy-2'-methyl-3'-butenyl)-pyrrolidine 在 sodium hydride 作用下， 以 四氢呋喃 、 paraffin 为溶剂， 反应 16.0h， 生成
  参考文献：
  名称：

  Synthése de la dolastatine 10 et de la [R-doe]-dolastatine 10

  摘要：

  A stepwise synthesis of dolastatin 10 starting from the dolaphenine residue is described. The chiral dola isoleuine and dolaproine residues were obtained by 5-step procedures from the corresponding N-Boc amino acid. The key steps are respectively the NaBH4 reduction of an allylic ketone and the addition of an achiral Z-crotylboronate on the N-Boc-L-prolinal. Peptidic couplings were efficiently realised with reagents developed in the laboratory.

  DOI：

  10.1016/s0040-4020(01)80692-x
• 作为产物：
  描述：

  BOC-L-脯氨酸 在 lithium aluminium tetrahydride 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 (2S,1'S,2'S)-N-(tert-butoxycarbonyl)-2-(1'-hydroxy-2'-methyl-3'-butenyl)-pyrrolidine
  参考文献：
  名称：

  Synthése de la dolastatine 10 et de la [R-doe]-dolastatine 10

  摘要：

  A stepwise synthesis of dolastatin 10 starting from the dolaphenine residue is described. The chiral dola isoleuine and dolaproine residues were obtained by 5-step procedures from the corresponding N-Boc amino acid. The key steps are respectively the NaBH4 reduction of an allylic ketone and the addition of an achiral Z-crotylboronate on the N-Boc-L-prolinal. Peptidic couplings were efficiently realised with reagents developed in the laboratory.

  DOI：

  10.1016/s0040-4020(01)80692-x

文献信息

• Substrate-controlled crotylborationt from N-(tert-butoxycarbonyl)amino aldehydes
  作者：Gilles Niel、Florence Roux、Ysadora Maisonnasse、Isabelle Maugras、Jo�l Poncet、Patrick Jouin

  DOI：10.1039/p19940001275

  日期：——

  Chiral or achiral (Z)-crotylorganoboron compounds add preferentially anti to N-(tert-butoxycarbonyl)-amino aldehydes. N-(tert-Butoxycarbonyl)prolinal 3 presents a remarkably high diastereofacial selectivity. Double stereodifferentiation, starting from compound 3, allows complete diastereoselective access to the gamma-amino-beta-hydroxy-alpha-methyl acid dolaproine 1 present in the antiproliferative dolastatin 10.
• Synthése de la dolastatine 10 et de la [R-doe]-dolastatine 10
  作者：Florence Roux、Isabelle Maugras、Joël Poncet、Gilles Niel、Patrick Jouin

  DOI：10.1016/s0040-4020(01)80692-x

  日期：1994.5

  A stepwise synthesis of dolastatin 10 starting from the dolaphenine residue is described. The chiral dola isoleuine and dolaproine residues were obtained by 5-step procedures from the corresponding N-Boc amino acid. The key steps are respectively the NaBH4 reduction of an allylic ketone and the addition of an achiral Z-crotylboronate on the N-Boc-L-prolinal. Peptidic couplings were efficiently realised with reagents developed in the laboratory.