N-(tert-butoxycarbonyl)-N-methyl-L-leucyl-L-alanine benzyl ester | 81135-24-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(tert-butoxycarbonyl)-N-methyl-L-leucyl-L-alanine benzyl ester
• 英文别名: N-(tert-butyloxycarbonyl)-N-methylleucylalanine benzyl ester；Boc-MeLeu-Ala-OBn；Boc-N(Me)Leu-Ala-OBn；benzyl (2S)-2-[[(2S)-4-methyl-2-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]pentanoyl]amino]propanoate
• CAS: 81135-24-2
• 化学式: C₂₂H₃₄N₂O₅
• 分子量: 406.522
• InChiKey: JURNPSDHKWCNBN-WMZOPIPTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  29
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  84.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(tert-butoxycarbonyl)-N-methyl-L-leucyl-L-alanine benzyl ester 在 碳酸氢钠 、 三氟乙酸 作用下， 以87%的产率得到N-methyl-L-leucyl-L-alanine benzyl ester
  参考文献：
  名称：

  环孢素的合成。总合成物'cyclosporin A'和'cyclosporin H'，两种真菌代谢物，从Tolypocladium inflatum GAMS物种中分离出来† ‡

  摘要：

  合成七肽H-MeBmt-Abu-Sar-MeLeu-Val-MeLeu-Ala-OBzl（20）以与先前描述的环孢素四肽序列Boc-D-Ala-MeLeu-MeVal-OH（21）偶联。然后将偶联的产物十一肽Boc-D-Ala-MeLeu-MeLeu-MeVal-MeBmt-abu-Sar-MeLeu-Val-MeLeu-Ala-OBzl（22）脱保护并环化为环孢霉素（1）。

  DOI：

  10.1002/hlca.19840670220
• 作为产物：
  描述：

  N-t-butoxycarbonyl-N-methyl-L-leucine 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 生成 N-(tert-butoxycarbonyl)-N-methyl-L-leucyl-L-alanine benzyl ester
  参考文献：
  名称：

  Synthesis of D-lysine8-cyclosporine A. Further characterization of BOP-Cl in the 2-7 hexapeptide fragment synthesis

  摘要：

  DOI：

  10.1021/jo00296a061

文献信息

• Synthesis of cyclosporine. Total syntheses of ?cyclosporin A? and ?cyclosporin H?, two fungal metabolites isolated from the speciesTolypocladium inflatum GAMS
  作者：Roland M. Wenger

  DOI：10.1002/hlca.19840670220

  日期：1984.3.14

  al-MeLeu-Ala-OBzl (20) was synthesized for coupling with the previously described cyclosporine tetrapeptide sequence Boc-D-Ala-MeLeu-MeVal-OH (21). The product of the coupling, the undecapeptide Boc-D-Ala-MeLeu-MeLeu-MeVal-MeBmt-abu-Sar-MeLeu-Val-MeLeu-Ala-OBzl (22), was then deprotected and cyclized to cyclosporine (1).

  合成七肽H-MeBmt-Abu-Sar-MeLeu-Val-MeLeu-Ala-OBzl（20）以与先前描述的环孢素四肽序列Boc-D-Ala-MeLeu-MeVal-OH（21）偶联。然后将偶联的产物十一肽Boc-D-Ala-MeLeu-MeLeu-MeVal-MeBmt-abu-Sar-MeLeu-Val-MeLeu-Ala-OBzl（22）脱保护并环化为环孢霉素（1）。
• Expanding the Limits of Isonitrile-Mediated Amidations: On the Remarkable Stereosubtleties of Macrolactam Formation from Synthetic <i>Seco</i>-Cyclosporins
  作者：Xiangyang Wu、Jennifer L. Stockdill、Peter K. Park、Samuel J. Danishefsky

  DOI：10.1021/ja2103372

  日期：2012.2.1

  The scope of isonitrile-mediated amide bond-forming reactions is further explored in this second-generation synthetic approach to cyclosporine (cyclosporin A). Both type I and type II amidations are utilized in this effort, allowing access to epimeric cyclosporins A and H from a single precursor by variation of the coupling reagents. This work lends deeper insight into the relative acylating ability of the formimidate carboxylate mixed anhydride (FCMA) intermediate, while shedding light on the far-reaching impact of remote stereochemical changes on the effective preorganization of seco-cyclosporins.
• COLUCCI, WILLIAM J.;TUNG, ROGER D.;PETRI, JOHN A.;RICH, DANIEL H., J. ORG. CHEM., 55,(1990) N, C. 2895-2903
  作者：COLUCCI, WILLIAM J.、TUNG, ROGER D.、PETRI, JOHN A.、RICH, DANIEL H.

  DOI：——

  日期：——
• Synthesis of D-lysine8-cyclosporine A. Further characterization of BOP-Cl in the 2-7 hexapeptide fragment synthesis
  作者：William J. Colucci、Roger D. Tung、John A. Petri、Daniel H. Rich

  DOI：10.1021/jo00296a061

  日期：1990.4