3-amino-N-butyloxycarbonyl-(S)-alanine methyl ester p-toluenesulfonate

• 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: 3-amino-N-butyloxycarbonyl-(S)-alanine methyl ester p-toluenesulfonate
• 英文别名: [(2S)-2-(butoxycarbonylamino)-3-methoxy-3-oxopropyl]azanium;4-methylbenzenesulfonate
• 化学式: C₇H₈O₃S*C₉H₁₈N₂O₄
• 分子量: 390.458
• InChiKey: OBVISRKPFHECPG-FJXQXJEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  158
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (R)-2-(3-(4-cyanophenyl)-4,5-dihydroisoxazol-5-yl)acetic acid 、 3-amino-N-butyloxycarbonyl-(S)-alanine methyl ester p-toluenesulfonate 在 氯化亚砜 、 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以82%的产率得到甲基N-(丁氧羰基)-3-({[(5R)-3-(4-氰基苯基)-4,5-二氢-1,2-恶唑-5-基]乙酰基}氨基)-L-丙氨酸酯
  参考文献：
  名称：

  The Enantiospecific Synthesis of an Isoxazoline. A RGD Mimic Platelet GPIIb/IIIa Antagonist

  摘要：

  A convergent, large-scale, chiral synthesis of isoxazoline 1 has been achieved in 37% overall yield and >99.6% optical purity, starting From L-asparagine and 4-cyanobenzaldehyde. Hofmann reaction of N-alpha-n-Boc-L-asparagine with iodosobenzene diacetate provides optically pure N-alpha-Boc-L-alpha,beta-diaminopropionic acid (8) in 75% yield. A process of lipase resolution-base catalyzed epimerization gives the single enantiomer 5. Reaction of acid 5 with amine 9 in the presence of thionyl chloride forms the framework of 1. A Pinner reaction of intermediate 4 in methyl acetate or anisole, followed by an amidination with ammonium acetate, gives optically pure product 1.

  DOI：

  10.1021/jo9612537
• 作为产物：
  描述：

  氯甲酸丁酯 在 氯化亚砜 、 碘苯二乙酸 、 sodium carbonate 作用下， 以 四氢呋喃 、 丙醇 、 乙酸甲酯 、 水 为溶剂， 反应 11.0h， 生成 3-amino-N-butyloxycarbonyl-(S)-alanine methyl ester p-toluenesulfonate
  参考文献：
  名称：

  The Enantiospecific Synthesis of an Isoxazoline. A RGD Mimic Platelet GPIIb/IIIa Antagonist

  摘要：

  A convergent, large-scale, chiral synthesis of isoxazoline 1 has been achieved in 37% overall yield and >99.6% optical purity, starting From L-asparagine and 4-cyanobenzaldehyde. Hofmann reaction of N-alpha-n-Boc-L-asparagine with iodosobenzene diacetate provides optically pure N-alpha-Boc-L-alpha,beta-diaminopropionic acid (8) in 75% yield. A process of lipase resolution-base catalyzed epimerization gives the single enantiomer 5. Reaction of acid 5 with amine 9 in the presence of thionyl chloride forms the framework of 1. A Pinner reaction of intermediate 4 in methyl acetate or anisole, followed by an amidination with ammonium acetate, gives optically pure product 1.

  DOI：

  10.1021/jo9612537
• 作为试剂：
  描述：

  [3-(4-cyano-phenyl)-4,5-dihydro-isoxazol-5-yl]-acetic acid 、 3-amino-N-butyloxycarbonyl-(S)-alanine methyl ester p-toluenesulfonate 在 3-amino-N-butyloxycarbonyl-(S)-alanine methyl ester p-toluenesulfonate 作用下， 以82的产率得到methyl 2-(butoxycarbonylamino)-3-[[2-[3-(4-cyanophenyl)-4,5-dihydro-1,2-oxazol-5-yl]acetyl]amino]propanoate
  参考文献：
  名称：

  J. Org. Chem. 1997, 62, 2466-2470

  摘要：

  DOI：

文献信息

• Synthesis of Cis and Trans Isomers of an Isoxazoline Ring-Hydroxylated Metabolite of Roxifiban, a Platelet Glycoprotein IIb/IIIa Receptor Antagonist
  作者：Douglas G. Batt、Gregory C. Houghton、Wayne F. Daneker、Prabhakar K. Jadhav

  DOI：10.1021/jo000755o

  日期：2000.11.1
• The Enantiospecific Synthesis of an Isoxazoline. A RGD Mimic Platelet GPIIb/IIIa Antagonist
  作者：Lin-hua Zhang、J. C. Chung、T. D. Costello、I. Valvis、P. Ma、S. Kauffman、R. Ward

  DOI：10.1021/jo9612537

  日期：1997.4.1

  A convergent, large-scale, chiral synthesis of isoxazoline 1 has been achieved in 37% overall yield and >99.6% optical purity, starting From L-asparagine and 4-cyanobenzaldehyde. Hofmann reaction of N-alpha-n-Boc-L-asparagine with iodosobenzene diacetate provides optically pure N-alpha-Boc-L-alpha,beta-diaminopropionic acid (8) in 75% yield. A process of lipase resolution-base catalyzed epimerization gives the single enantiomer 5. Reaction of acid 5 with amine 9 in the presence of thionyl chloride forms the framework of 1. A Pinner reaction of intermediate 4 in methyl acetate or anisole, followed by an amidination with ammonium acetate, gives optically pure product 1.
• J. Org. Chem. 1997, 62, 2466-2470
  作者：

  DOI：——

  日期：——