N-benzyloxycarbonyl-O-tosyl-(S)tyrosyl-glycyl-glycyl-(Z)dehydrophenylalanyl-(S)leucine methyl ester | 106111-08-4

• 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-benzyloxycarbonyl-O-tosyl-(S)tyrosyl-glycyl-glycyl-(Z)dehydrophenylalanyl-(S)leucine methyl ester
• 英文别名: (S,S)-Z-(O)Ts-Tyr-Gly2-ΔPhe-Leu-OMe
• CAS: 106111-08-4
• 化学式: C₄₄H₄₉N₅O₁₁S
• 分子量: 855.966
• InChiKey: FGCOUCOCHHNOQE-PFAAPKEUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.69
• 重原子数：
  61.0
• 可旋转键数：
  20.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  224.4
• 氢给体数：
  5.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  N-benzyloxycarbonyl-O-tosyl-(S)tyrosyl-glycyl-glycyl-(Z)dehydrophenylalanyl-(S)leucine methyl ester 在 [Rh((R,R)-DIPAMP)(COD)]BF₄ 、 氢气 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以90%的产率得到(S)-2-{2-[2-(2-{(S)-2-Benzyloxycarbonylamino-3-[4-(toluene-4-sulfonyloxy)-phenyl]-propionylamino}-acetylamino)-acetylamino]-3-phenyl-propionylamino}-4-methyl-pentanoic acid methyl ester
  参考文献：
  名称：

  Diastereoselective hydrogenation of monodehydro enkephalins controlled by chiral rhodium catalysts

  摘要：

  Protected (Z)dehydrophenylalanyl-Leu-enkephalin, (Z)dehydrotyrosyl-Leu-enkephalin and (Z)dehydrotyrosyl-(R)Ala2-Leu-enkephalin, have been synthesized. These compounds have been hydrogenated to give protected Leu-enkephalins in the presence of various chiral rhodium complexes. Deprotection of the product gave Leu-enkephalins or epimers, ytterbium in liquid ammonia allows smooth deprotection of NHCBz or OTs groups on small amounts of peptides. Strong stereocontrol could be achieved by suitable choice of the chiral catalyst. This method has good potential for stereospecific labelling of enkephalins and other small peptides.

  DOI：

  10.1016/s0957-4166(00)82083-2
• 作为产物：
  描述：

  Glycine,N-[O-[(4-methylphenyl)sulfonyl]-N-[(phenylmethoxy)carbonyl]-L-tyrosyl]-,ethyl ester 在 N-甲基吗啉 、 sodium hydroxide 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 20.0h， 生成 N-benzyloxycarbonyl-O-tosyl-(S)tyrosyl-glycyl-glycyl-(Z)dehydrophenylalanyl-(S)leucine methyl ester
  参考文献：
  名称：

  Diastereoselective hydrogenation of monodehydro enkephalins controlled by chiral rhodium catalysts

  摘要：

  Protected (Z)dehydrophenylalanyl-Leu-enkephalin, (Z)dehydrotyrosyl-Leu-enkephalin and (Z)dehydrotyrosyl-(R)Ala2-Leu-enkephalin, have been synthesized. These compounds have been hydrogenated to give protected Leu-enkephalins in the presence of various chiral rhodium complexes. Deprotection of the product gave Leu-enkephalins or epimers, ytterbium in liquid ammonia allows smooth deprotection of NHCBz or OTs groups on small amounts of peptides. Strong stereocontrol could be achieved by suitable choice of the chiral catalyst. This method has good potential for stereospecific labelling of enkephalins and other small peptides.

  DOI：

  10.1016/s0957-4166(00)82083-2

文献信息

• Synthesis of a protected monodehydro Leu-enkephalin and its hydrogenation catalyzed by chiral rhodium complexes
  作者：J.M. Nuzillard、J.C. Poulin、H.B. Kagan

  DOI：10.1016/s0040-4039(00)84699-7

  日期：1986.1