tert-butyl (2S)-4,4-difluoro-2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-[[(oxan-2-yloxyamino)-(phenylmethoxycarbonylamino)methylidene]amino]pentanoate | 910219-30-6

• 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: tert-butyl (2S)-4,4-difluoro-2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-[[(oxan-2-yloxyamino)-(phenylmethoxycarbonylamino)methylidene]amino]pentanoate
• CAS: 910219-30-6
• 化学式: C₂₈H₄₂F₂N₄O₈
• 分子量: 600.66
• InChiKey: XPQQWVMKHVCUKU-BGERDNNASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  42
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  146
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  tert-butyl (2S)-4,4-difluoro-2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-[[(oxan-2-yloxyamino)-(phenylmethoxycarbonylamino)methylidene]amino]pentanoate 、 三氟乙酸 在 茴香硫醚 作用下， 反应 5.0h， 以100%的产率得到4,4-difluoro-N^G-hydroxy-L-arginine
  参考文献：
  名称：

  N^G-Hydroxyguanidines from Primary Amines

  摘要：

  A concise and general method for the preparation of N-G-hydroxyguanidines from primary amines is reported. Using available and readily prepared materials, primary amines are converted to protected N-G-hydroxyguanidines in a one-pot procedure followed by deprotection under nonreducing conditions. The method has been successfully applied to a number of examples including a high-yielding preparation of N-G-hydroxy-L-arginine, the intermediate in the enzymatic conversion of L-arginine to nitric oxide and L-citrulline by nitric oxide synthase.

  DOI：

  10.1021/ol061454p
• 作为产物：
  描述：

  benzyloxycarbonyl isothiocyanate 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 tert-butyl (2S)-4,4-difluoro-2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-[[(oxan-2-yloxyamino)-(phenylmethoxycarbonylamino)methylidene]amino]pentanoate
  参考文献：
  名称：

  N^G-Hydroxyguanidines from Primary Amines

  摘要：

  A concise and general method for the preparation of N-G-hydroxyguanidines from primary amines is reported. Using available and readily prepared materials, primary amines are converted to protected N-G-hydroxyguanidines in a one-pot procedure followed by deprotection under nonreducing conditions. The method has been successfully applied to a number of examples including a high-yielding preparation of N-G-hydroxy-L-arginine, the intermediate in the enzymatic conversion of L-arginine to nitric oxide and L-citrulline by nitric oxide synthase.

  DOI：

  10.1021/ol061454p

文献信息

• <i>N</i>^G-Hydroxyguanidines from Primary Amines
  作者：Nathaniel I. Martin、Joshua J. Woodward、Michael A. Marletta

  DOI：10.1021/ol061454p

  日期：2006.8.1

  A concise and general method for the preparation of N-G-hydroxyguanidines from primary amines is reported. Using available and readily prepared materials, primary amines are converted to protected N-G-hydroxyguanidines in a one-pot procedure followed by deprotection under nonreducing conditions. The method has been successfully applied to a number of examples including a high-yielding preparation of N-G-hydroxy-L-arginine, the intermediate in the enzymatic conversion of L-arginine to nitric oxide and L-citrulline by nitric oxide synthase.