S(+)-2-amino-4-diethoxyphosphonobutanoic acid | 141894-89-5

• 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: S(+)-2-amino-4-diethoxyphosphonobutanoic acid
• 英文别名: (S)-2-amino-4-diethylphosphonobutyric acid；(2S)-2-amino-4-diethoxyphosphorylbutanoic acid
• CAS: 141894-89-5
• 化学式: C₈H₁₈NO₅P
• 分子量: 239.208
• InChiKey: GSFTXLYPUHBABL-ZETCQYMHSA-N

物化性质

• 沸点：
  386.5±37.0 °C(Predicted)
• 密度：
  1.219±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  98.8
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  S(+)-2-amino-4-diethoxyphosphonobutanoic acid 在 盐酸 作用下， 反应 6.0h， 以64%的产率得到L(+)-2-氨基-4-膦酰基丁酸
  参考文献：
  名称：

  Asymmetric synthesis of heteroorganic analogs of natural products. 6. (S)-?-amino-?-phosphonocarboxylic acids

  摘要：

  Alkylation, by omega-haloalkylphosphonates, of the Ni(II) complex of the Schiff base formed from glycine and (S)-2-N-(N1-benzylprolyl)-o-aminobenzophenone has been used for the asymmetric synthesis of (S)-2-amino-4-phosphonobutyric and (S)-2-amino-5-phosphonovaleric acids.

  DOI：

  10.1007/bf00869521
• 作为产物：
  描述：

  diethyl <4-hydroxy-3-(hydroxymethyl)butyl>phosphonate 在 palladium on activated charcoal jones reagent 、 二苯基膦叠氮化物 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 丙酮 为溶剂， 20.0~25.0 ℃ 、101.33 kPa 条件下， 反应 32.5h， 生成 S(+)-2-amino-4-diethoxyphosphonobutanoic acid
  参考文献：
  名称：

  Lipase-catalyzed enantioselective acylation of prochiral 2-(ω-phosphono)alkyl-1,3-propanediols: Application to the enantioselective synthesis of ω-phosphono-α-amino acids

  摘要：

  Lipase PS catalyzed acetylation of prochiral 2-(omega-phosphono)alkyl-1,3-propanediols 1a-c was found to proceed with high enantioselectivity. The applications of phosphonic chirons 2a-c thus obtained were illustrated by the stereocontrolled synthesis of omega-phosphono-alpha-amino acids such as L-AP-3, L-AP-4, and N-Boc-L-F(2)Pab(OEt)(2)-OH. Copyright (C) 1996 Published by Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00354-0

文献信息

• Synthesis of Optically Active 2-(<i>tert</i>-Butyloxycarbonylamino)-4-dialkoxyphosphorylbutanoate Protected Isosteres of<i>O</i>-Phosphonoserine for Peptide Synthesis
  作者：R. M. Valerio、P. F. Alewood、R. B. Johns

  DOI：10.1055/s-1988-27707

  日期：——

  The preparation of (S)-2-(tert-butoxycarbonylamino) -4-dialkoxyphosphorylbutanoate from (S)-aspartic acid is described.

  描述了从(S)-天冬氨酸制备(S)-2-(叔丁氧羰基氨基)-4-二烷氧基磷酰丁酸酯的过程。
• Soloshonok, Vadim A.; Belokon, Yuri N.; Kuzmina, Nadezhda A., Journal of the Chemical Society. Perkin transactions I, 1992, # 12, p. 1525 - 1530
  作者：Soloshonok, Vadim A.、Belokon, Yuri N.、Kuzmina, Nadezhda A.、Maleev, Victor I.、Svistunova, Nataly Yu.、et al.

  DOI：——

  日期：——
• Asymmetric synthesis of heteroorganic analogs of natural products. 6. (S)-?-amino-?-phosphonocarboxylic acids
  作者：V. A. Soloshonok、N. Yu. Svistunova、V. P. Kukhar'、V. A. Solodenko、N. A. Kuz'mina、A. B. Rozhenko、S. V. Galushko、I. P. Shishkina、A. O. Gudima、Yu. N. Belokon'

  DOI：10.1007/bf00869521

  日期：1992.2

  Alkylation, by omega-haloalkylphosphonates, of the Ni(II) complex of the Schiff base formed from glycine and (S)-2-N-(N1-benzylprolyl)-o-aminobenzophenone has been used for the asymmetric synthesis of (S)-2-amino-4-phosphonobutyric and (S)-2-amino-5-phosphonovaleric acids.
• A Novel Asymmetric Synthesis of S-(+)-2-Amino-4-Phosphonobutanoic Acid
  作者：Xian-Yun Jiao、Wan-Yi Chen、Bing-Fang Hu

  DOI：10.1080/00397919208021103

  日期：1992.4

  A novel asymmetric synthetic route to S(+)-2-amino-4-phosphonobutanoic acid through the cyclic condensation of ethyl-4-diethoxyphosphonyl-2-oxo-butanoate with L-erythro-(+)-1,2-diphenyl-2-hydroxyethylamine, followed by reduction and hydrolysis is described.
• Lipase-catalyzed enantioselective acylation of prochiral 2-(ω-phosphono)alkyl-1,3-propanediols: Application to the enantioselective synthesis of ω-phosphono-α-amino acids
  作者：Tsutomu Yokomatsu、Mutsumi Sato、Shiroshi Shibuya

  DOI：10.1016/0957-4166(96)00354-0

  日期：1996.9

  Lipase PS catalyzed acetylation of prochiral 2-(omega-phosphono)alkyl-1,3-propanediols 1a-c was found to proceed with high enantioselectivity. The applications of phosphonic chirons 2a-c thus obtained were illustrated by the stereocontrolled synthesis of omega-phosphono-alpha-amino acids such as L-AP-3, L-AP-4, and N-Boc-L-F(2)Pab(OEt)(2)-OH. Copyright (C) 1996 Published by Elsevier Science Ltd