cyclo-N^ε-(benzyloxycarbonyl)-L-lysyl-L-valyl-(2-azido-3-undecyl-β-alanyl)glycine | 440353-79-7

• 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: cyclo-N^ε-(benzyloxycarbonyl)-L-lysyl-L-valyl-(2-azido-3-undecyl-β-alanyl)glycine
• 英文别名: cyclo[Gly-Lys(Cbz)(Cbz)-Val-bAla(2R-N3,3R-undecyl)]；benzyl N-[4-[(5S,8S,11R,12R)-12-azido-3,6,9,13-tetraoxo-8-propan-2-yl-11-undecyl-1,4,7,10-tetrazacyclotridec-5-yl]butyl]carbamate
• CAS: 440353-79-7
• 化学式: C₃₅H₅₆N₈O₆
• 分子量: 684.88
• InChiKey: ALOMWMWQUGRRHK-HNRHMXCFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  49
• 可旋转键数：
  20
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  169
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  cyclo-N^ε-(benzyloxycarbonyl)-L-lysyl-L-valyl-(2-azido-3-undecyl-β-alanyl)glycine 在 10percent Pd/C 甲酸 、 氢气 、 氢溴酸 作用下， 以 二氯甲烷 、 水 、 溶剂黄146 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 61.0h， 以45%的产率得到cyclo-L-lysyl-L-valyl-(2-amino-3-undecyl-β-alanyl)glycine dihydrochloride
  参考文献：
  名称：

  An Enantioselective Synthesis of Differentially Protected erythro-α,β-Diamino Acids and Its Application to the Synthesis of an Analogue of Rhodopeptin B5

  摘要：

  Methodology for the enantioselective synthesis of differentially protected erythro-alpha,beta-diamino acids from N-tosyloxy beta-lactams is reported. The requisite N-tosyloxy beta-lactams are readily available from simple beta-keto esters. The reported approach is flexible and compatible with a variety of functional groups. The synthetic utility of the method is demonstrated through its application to the preparation of an analogue of the antifungal cyclic peptide rhodopeptin B5.

  DOI：

  10.1021/jo016276m
• 作为产物：
  描述：

  Boc-Lys(Cbz)(Cbz)-Val-OH 在 lithium hydroxide 、 N-羟基-7-氮杂苯并三氮唑 、 二苯基膦叠氮化物 、 碳酸氢钠 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 111.0h， 生成 cyclo-N^ε-(benzyloxycarbonyl)-L-lysyl-L-valyl-(2-azido-3-undecyl-β-alanyl)glycine
  参考文献：
  名称：

  An Enantioselective Synthesis of Differentially Protected erythro-α,β-Diamino Acids and Its Application to the Synthesis of an Analogue of Rhodopeptin B5

  摘要：

  Methodology for the enantioselective synthesis of differentially protected erythro-alpha,beta-diamino acids from N-tosyloxy beta-lactams is reported. The requisite N-tosyloxy beta-lactams are readily available from simple beta-keto esters. The reported approach is flexible and compatible with a variety of functional groups. The synthetic utility of the method is demonstrated through its application to the preparation of an analogue of the antifungal cyclic peptide rhodopeptin B5.

  DOI：

  10.1021/jo016276m

文献信息

• An Enantioselective Synthesis of Differentially Protected <i>erythro</i>-α,β-Diamino Acids and Its Application to the Synthesis of an Analogue of Rhodopeptin B5
  作者：Timothy B. Durham、Marvin J. Miller

  DOI：10.1021/jo016276m

  日期：2003.1.1

  Methodology for the enantioselective synthesis of differentially protected erythro-alpha,beta-diamino acids from N-tosyloxy beta-lactams is reported. The requisite N-tosyloxy beta-lactams are readily available from simple beta-keto esters. The reported approach is flexible and compatible with a variety of functional groups. The synthetic utility of the method is demonstrated through its application to the preparation of an analogue of the antifungal cyclic peptide rhodopeptin B5.