N-(tert-Butoxycarbonyl)-dolaproinyl-(6R)-dolaphenine | 153668-71-4

• 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: N-(tert-Butoxycarbonyl)-dolaproinyl-(6R)-dolaphenine
• 英文别名: Boc-Dap-(R)-Doe；tert-butyl (2S)-2-[(1R,2R)-1-methoxy-2-methyl-3-oxo-3-[[(1R)-2-phenyl-1-(1,3-thiazol-2-yl)ethyl]amino]propyl]pyrrolidine-1-carboxylate
• CAS: 153668-71-4
• 化学式: C₂₅H₃₅N₃O₄S
• 分子量: 473.637
• InChiKey: IUCQRIRVQMEYPP-AYWYSENESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(tert-Butoxycarbonyl)-dolaproinyl-(6R)-dolaphenine 在 bromo-tris-dimethylamino-phosphonium hexafluorophosphate 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 Z-Val-Dil-Dap-(R)-Doe
  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：

  (2S,1’R,2’S)-N-(叔丁氧基羰基)-2-(1’-羟基-2’-甲基-3’-丁烯)-吡咯烷 在 ruthenium(IV) oxide 、 potassium permanganate 、 sodium periodate 、 sodium hydride 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 四氯化碳 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 、 叔丁醇 为溶剂， 反应 31.25h， 生成 N-(tert-Butoxycarbonyl)-dolaproinyl-(6R)-dolaphenine
  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

• The Dolastatins. 22. Synthesis Of Boc-Dolaproinyl Dolaphenine and Four Related Chiral Isomers
  作者：George R. Pettit、Jozsef Barkoczy、Jayaram K. Srirangam、Sheo Bux Singh、Delbert L. Herald、Michael D. Williams、Darko Kantoci、Fiona Hogan、Thomas L. Groy

  DOI：10.1021/jo00090a009

  日期：1994.6

  Synthesis of the dolastatin 10 (1) dipeptide segment N-(tert-butoxycarbonyl)-dolaproinyl-dolaphenine (2, Boc-Dap-Doe) and four chiral isomers (3-5, 13) has been summarized. Formation of the amide bond was readily accomplished employing diethyl cyanophosphonate. The stereochemical assignments for Boc-Dap-Doe (2) and Boc-Dap-(6R)-Doe (3) were confirmed by X-ray crystal structure analyses.
• The Dolastatins. 21. Synthesis, X-ray Crystal Structure, and Molecular Modeling of (6R)-Isodolastatin 10
  作者：George R. Pettit、Jayaram K. Srirangam、Delbert L. Herald、Ernest Hamel

  DOI：10.1021/jo00100a001

  日期：1994.10

  A practical synthesis of (GR)-isodolastatin 10 (1b) was devised, the X-ray crystal structure was determined, and this chiral isomer was found to have antineoplastic activity comparable to dolastatin 10 (1a).
• 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.