methyl (2S)-3-hydroxy-2-[[(2S,4R)-2-methyl-4-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoyl]amino]propanoate | 199930-79-5

• 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: methyl (2S)-3-hydroxy-2-[[(2S,4R)-2-methyl-4-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoyl]amino]propanoate
• CAS: 199930-79-5
• 化学式: C₁₅H₂₈N₂O₆
• 分子量: 332.397
• InChiKey: BTHLUKOHNQQVKM-AXFHLTTASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  114
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (2S)-3-hydroxy-2-[[(2S,4R)-2-methyl-4-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoyl]amino]propanoate 在 伯吉斯试剂 作用下， 以 四氢呋喃 为溶剂， 反应 10.25h， 生成 2-((1S,3R)-3-tert-Butoxycarbonylamino-1-methyl-butyl)-oxazole-4-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis of the C₂₆−C₃₂ Oxazole Fragment of Calyculin C:  A Test Case for Oxazole Syntheses

  摘要：

  The synthesis of the C-26-C-32 oxazole fragment 4 and its C-32 epimer 20 of serine/threonine protein phosphatase PP1 and PP2A inhibitor calyculin C is presented. The syn methyl arrangement in 4 was established through cyclic stereocontrol. Several methods for oxidizing the intermediate oxazolines 18 and 19 to the finished oxazole fragments were explored. The best results were obtained with oxidations proceeding through the corresponding ester enolate when the carbamate NH side chain was temporarily protected with a TMS group, or with CuBr2/DBU/HMTA-based oxidations. The finished oxazole fragment 4 was obtained in 21% overall yield, starting from Boc-D-alaninal.

  DOI：

  10.1021/jo971167m
• 作为产物：
  描述：

  L-丝氨酸甲酯盐酸盐 、 (4R)-2-methyl-4-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoic acid 在 N-甲基吗啉 、 氯甲酸异丁酯 作用下， 生成 methyl (2S)-3-hydroxy-2-[[(2S,4R)-2-methyl-4-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoyl]amino]propanoate 、 methyl (2S)-3-hydroxy-2-[[(2R,4R)-2-methyl-4-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoyl]amino]propanoate
  参考文献：
  名称：

  Synthesis of the C₂₆−C₃₂ Oxazole Fragment of Calyculin C:  A Test Case for Oxazole Syntheses

  摘要：

  The synthesis of the C-26-C-32 oxazole fragment 4 and its C-32 epimer 20 of serine/threonine protein phosphatase PP1 and PP2A inhibitor calyculin C is presented. The syn methyl arrangement in 4 was established through cyclic stereocontrol. Several methods for oxidizing the intermediate oxazolines 18 and 19 to the finished oxazole fragments were explored. The best results were obtained with oxidations proceeding through the corresponding ester enolate when the carbamate NH side chain was temporarily protected with a TMS group, or with CuBr2/DBU/HMTA-based oxidations. The finished oxazole fragment 4 was obtained in 21% overall yield, starting from Boc-D-alaninal.

  DOI：

  10.1021/jo971167m