(R)-tert-butyl 2-((2S,6R,Z)-6-(N-tert-butyloxycarbonyl)amino-2-(N-benzyl-N-benzyloxycarbonyl)amino-7-hydroxyhept-4-enamido)propanoate | 815584-73-7

• 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: (R)-tert-butyl 2-((2S,6R,Z)-6-(N-tert-butyloxycarbonyl)amino-2-(N-benzyl-N-benzyloxycarbonyl)amino-7-hydroxyhept-4-enamido)propanoate
• 英文别名: tert-butyl (2R)-2-[[(Z,2S,6R)-2-[benzyl(phenylmethoxycarbonyl)amino]-7-hydroxy-6-[(2-methylpropan-2-yl)oxycarbonylamino]hept-4-enoyl]amino]propanoate
• CAS: 815584-73-7
• 化学式: C₃₄H₄₇N₃O₈
• 分子量: 625.762
• InChiKey: WRFOFRIKKZKJTC-YJVBJRPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  45
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  144
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (R)-tert-butyl 2-((2S,6R,Z)-6-(N-tert-butyloxycarbonyl)amino-2-(N-benzyl-N-benzyloxycarbonyl)amino-7-hydroxyhept-4-enamido)propanoate 在 palladium dihydroxide 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.32 kPa 条件下， 反应 48.0h， 生成 (R)-2-((2S,6R)-2-Amino-6-tert-butoxycarbonylamino-7-hydroxy-heptanoylamino)-propionic acid tert-butyl ester
  参考文献：
  名称：

  An Efficient RCM-Based Synthesis of Orthogonally Protected meso-DAP and FK565

  摘要：

  A condensation-ring-close-ring-open sequence was employed for the synthesis of orthogonally protected meso-2,6-diaminopimelic acid, starting from easily accessible chiral synthons. Condensation of suitably protected L-allylglycine and D-vinylglycinol derivatives was followed by Grubbs' ring-closing metathesis to generate the key lactam intermediate. This strategy has been applied to a concise total synthesis of the potent immunostimulatory peptide FK565.

  DOI：

  10.1021/jo0485738
• 作为产物：
  描述：

  (2S)-2-benzylaminopent-4-enoic acid methyl ester 在 吡啶 、 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 4-二甲氨基吡啶 、 lithium hydroxide 、 sodium hydroxide 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 sodium carbonate 、 三乙胺 、 3-(二乙氧基邻酰氧基)-1,2,3-苯并三嗪-4-酮 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 102.0h， 生成 (R)-tert-butyl 2-((2S,6R,Z)-6-(N-tert-butyloxycarbonyl)amino-2-(N-benzyl-N-benzyloxycarbonyl)amino-7-hydroxyhept-4-enamido)propanoate
  参考文献：
  名称：

  An Efficient RCM-Based Synthesis of Orthogonally Protected meso-DAP and FK565

  摘要：

  A condensation-ring-close-ring-open sequence was employed for the synthesis of orthogonally protected meso-2,6-diaminopimelic acid, starting from easily accessible chiral synthons. Condensation of suitably protected L-allylglycine and D-vinylglycinol derivatives was followed by Grubbs' ring-closing metathesis to generate the key lactam intermediate. This strategy has been applied to a concise total synthesis of the potent immunostimulatory peptide FK565.

  DOI：

  10.1021/jo0485738

文献信息

• An Efficient RCM-Based Synthesis of Orthogonally Protected <i>m</i><i>eso</i>-DAP and FK565
  作者：Juan R. Del Valle、Murray Goodman

  DOI：10.1021/jo0485738

  日期：2004.12.1

  A condensation-ring-close-ring-open sequence was employed for the synthesis of orthogonally protected meso-2,6-diaminopimelic acid, starting from easily accessible chiral synthons. Condensation of suitably protected L-allylglycine and D-vinylglycinol derivatives was followed by Grubbs' ring-closing metathesis to generate the key lactam intermediate. This strategy has been applied to a concise total synthesis of the potent immunostimulatory peptide FK565.