(R)-3-<4-<2-<<(1,1-Dimethylethoxy)carbonyl>amino>-2-<<<<<(2-bromoethyl)oxy>carbonyl>methyl>amino>carbonyl>ethyl>phenoxy>-N-<(phenylmethoxy)carbonyl>-D-phenylglycine α-methyl ester | 139377-46-1

• 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: (R)-3-<4-<2-<<(1,1-Dimethylethoxy)carbonyl>amino>-2-<<<<<(2-bromoethyl)oxy>carbonyl>methyl>amino>carbonyl>ethyl>phenoxy>-N-<(phenylmethoxy)carbonyl>-D-phenylglycine α-methyl ester
• 英文别名: O-D-3-<1-<-2-oxo-2-methoxyethyl>phenyl>-D-N-<(1,1-dimethylethoxy)carbonyl>tyrosylglycine 2-bromoethyl ester；O-D-3-(1-{[N-(benzyloxycarbonyl)amino]-2-oxo-2-methoxyethyl}phenyl)-D-N-[(1,1-dimethylethoxy)carbonyl]tyrosylglycine 2-bromoethyl ester；methyl (2R)-2-[3-[4-[(2R)-3-[[2-(2-bromoethoxy)-2-oxoethyl]amino]-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-oxopropyl]phenoxy]phenyl]-2-(phenylmethoxycarbonylamino)acetate
• CAS: 139377-46-1
• 化学式: C₃₅H₄₀BrN₃O₁₀
• 分子量: 742.621
• InChiKey: RCMZEXPKPXOTHG-PQHLKRTFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  49
• 可旋转键数：
  20
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  168
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (R)-3-<4-<2-<<(1,1-Dimethylethoxy)carbonyl>amino>-2-<<<<<(2-bromoethyl)oxy>carbonyl>methyl>amino>carbonyl>ethyl>phenoxy>-N-<(phenylmethoxy)carbonyl>-D-phenylglycine α-methyl ester 在 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 7.0h， 以82%的产率得到(R)-3-<4-<2-<<(1,1-Dimethylethoxy)carbonyl>amino>-2-<<<<<(2-iodoethyl)oxy>carbonyl>methyl>amino>carbonyl>ethyl>phenoxy>-N-<(phenylmethoxy)carbonyl>-D-phenylglycine α-methyl ester
  参考文献：
  名称：

  Some Studies on the Uses of 2-Bromoethyl and 2-Iodoethyl Ester Blocking Groups in Peptide Synthesis: Samarium Diiodide-Mediated Deprotection

  摘要：

  DOI：

  10.1021/jo00087a053
• 作为产物：
  描述：

  (4R,5S)-4-chloro-1-<3-oxo-3-(2-oxo-4-methyl-5-phenyl-3-oxazolidinyl)propyl>benzene 在 palladium on activated charcoal lithium hydroxide 、 2,4,6-三异丙基苯磺酰叠氮化物 、 氢气 、 双氧水 、 双(三甲基硅烷基)氨基钾 、 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 水 、 乙酸乙酯 为溶剂， 反应 22.03h， 生成 (R)-3-<4-<2-<<(1,1-Dimethylethoxy)carbonyl>amino>-2-<<<<<(2-bromoethyl)oxy>carbonyl>methyl>amino>carbonyl>ethyl>phenoxy>-N-<(phenylmethoxy)carbonyl>-D-phenylglycine α-methyl ester
  参考文献：
  名称：

  Model studies on the synthesis of carboxylate-binding pocket analogs of vancomycin using arene-ruthenium chemistry

  摘要：

  Preparation of several protected (D)-chlorophenylalanine derivatives in high optical purity and their complex formation with the [RuCp]+ moiety are described. The complexation reaction, as well as subsequent photochemical decomplexations, proceeds with retention of optical purity. Reactions of these chloroarene complexes with 3-hydroxyphenylglycine derivatives proceed under mild conditions to give aryl ether-ruthenium complexes, which can be converted to diaryl ethers in which both aromatic rings have protected amino acid or peptide side chains. Efforts to effect cycloamidation to give vancomycin carboxylate-binding pocket analogues, using a number of known coupling reagents, were unsuccessful.

  DOI：

  10.1021/jo00032a028