5-[[bis[[(1,1-dimethoxy)carbonyl]amino]methylene]amino]-2-hydroxypentanoic acid | 262601-07-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 5-[[bis[[(1,1-dimethoxy)carbonyl]amino]methylene]amino]-2-hydroxypentanoic acid
• 英文别名: 5-[Bis[(2-methylpropan-2-yl)oxycarbonylamino]methylideneamino]-2-hydroxypentanoic acid
• CAS: 262601-07-0
• 化学式: C₁₆H₂₉N₃O₇
• 分子量: 375.422
• InChiKey: JXXPHAOBRRDAMN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  26
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  147
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5-[[bis[[(1,1-dimethoxy)carbonyl]amino]methylene]amino]-2-hydroxypentanoic acid 在 1-羟基苯并三唑 、 戴斯-马丁氧化剂 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 12.5h， 生成 (E)-5-[[bis[[(1,1-dimethoxy)carbonyl]amino]methylene]amino]-2-oxopentanoyl-N-[2-(4-acetoxyphenyl)ethenyl]glycinamide
  参考文献：
  名称：

  Total Syntheses of (±)-Anchinopeptolide D and (±)-Cycloanchinopeptolide D

  摘要：

  The first synthesis of (+/-)-anchinopeptolide D (4) has been accomplished in seven steps in 10% overall yield from octopamine hydrochloride (17), N-(Boc)glycine (16), and 5-amino-2-hydroxypentanoic acid (22). The key step is the aldol dimerization and hemiaminal formation of cr-keto amide 26, which gives primarily protected anchinopeptolide D 27 under kinetically controlled conditions. Cycloanchinopeptolide D (31) has been prepared by the unprecedented head-to-head photodimerization of the two hydroxystyrylamides of 4 using the hydrophobic effect in water to force the two side chains into close proximity so that [2 + 2] cycloaddition is faster than trans to cis double bond isomerization. Coupling of amine 21 with pyroglutamic acid affords the naturally occurring tripeptide 35, which had been assigned glutamic acid structure 34.

  DOI：

  10.1021/jo991454l
• 作为产物：
  描述：

  5-amino-2-hydroxypentanoic acid 、 1-[(tert-butyloxycarbonylamino)-(tert-butyloxycarbonylimino)-methyl]-1H-pyrazole 在 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 formamide 为溶剂， 反应 18.0h， 以77%的产率得到5-[[bis[[(1,1-dimethoxy)carbonyl]amino]methylene]amino]-2-hydroxypentanoic acid
  参考文献：
  名称：

  Total Syntheses of (±)-Anchinopeptolide D and (±)-Cycloanchinopeptolide D

  摘要：

  The first synthesis of (+/-)-anchinopeptolide D (4) has been accomplished in seven steps in 10% overall yield from octopamine hydrochloride (17), N-(Boc)glycine (16), and 5-amino-2-hydroxypentanoic acid (22). The key step is the aldol dimerization and hemiaminal formation of cr-keto amide 26, which gives primarily protected anchinopeptolide D 27 under kinetically controlled conditions. Cycloanchinopeptolide D (31) has been prepared by the unprecedented head-to-head photodimerization of the two hydroxystyrylamides of 4 using the hydrophobic effect in water to force the two side chains into close proximity so that [2 + 2] cycloaddition is faster than trans to cis double bond isomerization. Coupling of amine 21 with pyroglutamic acid affords the naturally occurring tripeptide 35, which had been assigned glutamic acid structure 34.

  DOI：

  10.1021/jo991454l

文献信息

• Total Syntheses of (±)-Anchinopeptolide D and (±)-Cycloanchinopeptolide D
  作者：Barry B. Snider、Fengbin Song、Bruce M. Foxman

  DOI：10.1021/jo991454l

  日期：2000.2.1

  The first synthesis of (+/-)-anchinopeptolide D (4) has been accomplished in seven steps in 10% overall yield from octopamine hydrochloride (17), N-(Boc)glycine (16), and 5-amino-2-hydroxypentanoic acid (22). The key step is the aldol dimerization and hemiaminal formation of cr-keto amide 26, which gives primarily protected anchinopeptolide D 27 under kinetically controlled conditions. Cycloanchinopeptolide D (31) has been prepared by the unprecedented head-to-head photodimerization of the two hydroxystyrylamides of 4 using the hydrophobic effect in water to force the two side chains into close proximity so that [2 + 2] cycloaddition is faster than trans to cis double bond isomerization. Coupling of amine 21 with pyroglutamic acid affords the naturally occurring tripeptide 35, which had been assigned glutamic acid structure 34.