(2R,6S)-6-(N-benzyl-N-benzyloxycarbonyl)amino-2-(N-tert-butoxycarbonyl)amino-7-methoxycarbonylheptanoic acid | 815584-72-6

• 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: (2R,6S)-6-(N-benzyl-N-benzyloxycarbonyl)amino-2-(N-tert-butoxycarbonyl)amino-7-methoxycarbonylheptanoic acid
• 英文别名: (2R,6S)-6-[benzyl(phenylmethoxycarbonyl)amino]-7-methoxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]-7-oxoheptanoic acid
• CAS: 815584-72-6
• 化学式: C₂₈H₃₆N₂O₈
• 分子量: 528.602
• InChiKey: VXHJSCKKFLKJSX-PKTZIBPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  38
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  132
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2R,6S)-6-(N-benzyl-N-benzyloxycarbonyl)amino-2-(N-tert-butoxycarbonyl)amino-7-methoxycarbonylheptanoic acid 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成
  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 sodium chlorite 、 Crabtree's catalyst 吡啶 、 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 4-二甲氨基吡啶 、 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 lithium hydroxide 、 sodium hydroxide 、 sodium hypochlorite 、 sodium dihydrogenphosphate 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 氢气 、 sodium carbonate 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 20.0~40.0 ℃ 、101.33 kPa 条件下， 反应 123.0h， 生成 (2R,6S)-6-(N-benzyl-N-benzyloxycarbonyl)amino-2-(N-tert-butoxycarbonyl)amino-7-methoxycarbonylheptanoic acid
  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.