N-tert-butoxycarbonyl-L-4-bromophenylalanyl-N-propargyl-O-benzyl-L-serine methyl ester | 923293-29-2

• 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-L-4-bromophenylalanyl-N-propargyl-O-benzyl-L-serine methyl ester
• 英文别名: Boc-Phe(4-Br)-N(prop-2-ynyl)Ser(Bn)-OMe；methyl (2S)-2-[[(2S)-3-(4-bromophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]-prop-2-ynylamino]-3-phenylmethoxypropanoate
• CAS: 923293-29-2
• 化学式: C₂₈H₃₃BrN₂O₆
• 分子量: 573.484
• InChiKey: ZAWXXPHJWNFOJH-ZEQRLZLVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  37
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  94.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-tert-butoxycarbonyl-L-4-bromophenylalanyl-N-propargyl-O-benzyl-L-serine methyl ester 在 硼烷四氢呋喃络合物 、 copper(II) sulfate 、 sodium ascorbate 、 2-叔丁基亚氨基-2-二乙基氨基-1,3-二甲基全氢-1,3,2-二氮杂磷 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 39.72h， 生成 (3S,6S)-3-(benzyloxymethyl)-6-(4-bromobenzyl)-4-[1-((S)-1-hydroxy-3-phenyl-prop-2-yl)-1H-1,2,3-triazol-4-ylmethyl]-1-(3-hydroxypropyl)piperazine-2,5-dione
  参考文献：
  名称：

  Synthesis of Functionalized, Unsymmetrical 1,3,4,6-Tetrasubstituted 2,5-Diketopiperazines

  摘要：

  A general and efficient method for the synthesis of unsymmetrical 1,3,4,6-tetrasubstituted 2,5-diketo- piperazines (DKPs) is described. Cyclization of N-amide alkylated dipeptide methyl esters, followed by alkylation, furnished the corresponding tetrasubstituted DKPs in good overall yields. The influence of steric hindrance in the alkylation reactions appeared to be of lesser importance as long as reactive alkylating agents were used. Furthermore, we have demonstrated the use of tetrasubstituted DKPs as a scaffold for further chemical manipulations to produce novel DKPs with desired properties.

  DOI：

  10.1021/jo0619635
• 作为产物：
  描述：

  N-propargyl-O-benzyl-L-serine methyl ester 、 Boc-L-4-溴苯丙氨酸 在 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 二氯甲烷 为溶剂， 以72%的产率得到N-tert-butoxycarbonyl-L-4-bromophenylalanyl-N-propargyl-O-benzyl-L-serine methyl ester
  参考文献：
  名称：

  Synthesis of Functionalized, Unsymmetrical 1,3,4,6-Tetrasubstituted 2,5-Diketopiperazines

  摘要：

  A general and efficient method for the synthesis of unsymmetrical 1,3,4,6-tetrasubstituted 2,5-diketo- piperazines (DKPs) is described. Cyclization of N-amide alkylated dipeptide methyl esters, followed by alkylation, furnished the corresponding tetrasubstituted DKPs in good overall yields. The influence of steric hindrance in the alkylation reactions appeared to be of lesser importance as long as reactive alkylating agents were used. Furthermore, we have demonstrated the use of tetrasubstituted DKPs as a scaffold for further chemical manipulations to produce novel DKPs with desired properties.

  DOI：

  10.1021/jo0619635