(3S)-N-(benzyloxycarbonyl)-3-amino-2-hydroxy-4-phenylbutanoic acid | 222848-56-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3S)-N-(benzyloxycarbonyl)-3-amino-2-hydroxy-4-phenylbutanoic acid
• 英文别名: Z-(2S,3S)-AHPA；(3S)-3-{[(benzyloxy)carbonyl]amino}-2-hydroxy-4-phenylbutanoic acid；(3S)-2-hydroxy-4-phenyl-3-(phenylmethoxycarbonylamino)butanoic acid
• CAS: 222848-56-8
• 化学式: C₁₈H₁₉NO₅
• 分子量: 329.353
• InChiKey: JXJYTERRLRAUSF-VYRBHSGPSA-N

物化性质

• 沸点：
  581.9±50.0 °C(Predicted)
• 密度：
  1.295±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  95.9
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3S)-N-(benzyloxycarbonyl)-3-amino-2-hydroxy-4-phenylbutanoic acid 在 palladium on activated charcoal 氢气 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 三乙胺 作用下， 以 乙酸乙酯 、 乙腈 为溶剂， 反应 0.25h， 生成 (2S)-N-(3-{(2S)-2-[N-(tert-Butyl)carbamoyl]pyrrolidinyl}(1S,2S)-2-hydroxy-3-oxo-1-benzylpropyl)-2-{(2S)-2-[(phenylmethoxy)carbonylamino]propanoylamino}-3-methylbutanamide
  参考文献：
  名称：

  Development of a New Type of Protease Inhibitors, Efficacious against FIV and HIV Variants

  摘要：

  Based on the structural analysis of FIV protease and drug-resistant HIV proteases and molecular modeling, a new type of inhibitors with a small P3 residue has been developed. These inhibitors are effective against HIV and its drug-resistant mutants, as well as SIV and FIV. Modification of existing HIV protease inhibitors by reducing the size of the P3 residue has the same effect. This finding provides a new strategy for the development of HIV protease inhibitors effective against the wild-type and drug-resistant mutants. It further supports the use of FIV protease as a useful model for drug-resistant HIV proteases, which often have a more constricted binding region for the P3 group or the combined P3 and P1 groups.

  DOI：

  10.1021/ja982893p
• 作为产物：
  描述：

  (2RS,3S)-3-(benzyloxycarbonyl)amino-2-hydroxy-4-phenylbutanenitrile 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 生成 (3S)-N-(benzyloxycarbonyl)-3-amino-2-hydroxy-4-phenylbutanoic acid
  参考文献：
  名称：

  Development of a New Type of Protease Inhibitors, Efficacious against FIV and HIV Variants

  摘要：

  Based on the structural analysis of FIV protease and drug-resistant HIV proteases and molecular modeling, a new type of inhibitors with a small P3 residue has been developed. These inhibitors are effective against HIV and its drug-resistant mutants, as well as SIV and FIV. Modification of existing HIV protease inhibitors by reducing the size of the P3 residue has the same effect. This finding provides a new strategy for the development of HIV protease inhibitors effective against the wild-type and drug-resistant mutants. It further supports the use of FIV protease as a useful model for drug-resistant HIV proteases, which often have a more constricted binding region for the P3 group or the combined P3 and P1 groups.

  DOI：

  10.1021/ja982893p

文献信息

• Synthesis and Human Immunodeficiency Virus(HIV)-1 protease Inhibitory Activity of Tripeptide Analogues Containing a Dioxoethylene Moiety.
  作者：Tomoyuki KITAZAKI、Tsuneo ASANO、Koichi KATO、Shoji KISHIMOTO、Katsumi ITOH

  DOI：10.1248/cpb.42.2636

  日期：——

  Tripeptide analogues 2 and 3 containing a dioxoethylene moiety were designed based on the characteristic structure of the naturally occurring human immunodeficiency virus (HIV)-1 protease inhibitors RPI-856 A, B, C and D (1). The compounds (2, 3) prepared showed high inhibitory activity, comparable to that of RPI-856 A, against HIV-1 protease in vitro.

  根据天然存在的人类免疫缺陷病毒（HIV）-1 蛋白酶抑制剂 RPI-856 A、B、C 和 D (1)的特征结构，设计了含有二氧乙烯分子的三肽类似物 2 和 3。所制备的化合物（2、3）在体外对 HIV-1 蛋白酶具有很高的抑制活性，与 RPI-856 A 相当。
• Synthesis of a cis-conformationally restricted peptide bond isostere and its application to the inhibition of the HIV-1 protease
  作者：Andrew D. Abell、Glenn J. Foulds

  DOI：10.1039/a702458d

  日期：——

  A synthesis of a new, tetrazole-based, cis-constrained hydroxyethylamine peptide bond isostere is reported. This has been used to produce a new class of HIV-1 protease inhibitor.

  报告了一种新的、基于四氮唑的顺式受约束羟乙基胺肽键异构体的合成。该化合物已被用于生产一种新型的 HIV-1 蛋白酶抑制剂。
• Chemoselective Catalytic Oxidation of 1,2-Diols to α-Hydroxy Acids Controlled by TEMPO–ClO₂ Charge-Transfer Complex
  作者：Keisuke Furukawa、Masatoshi Shibuya、Yoshihiko Yamamoto

  DOI：10.1021/acs.orglett.5b01003

  日期：2015.5.1

  Chemoselective catalytic oxidation from 1,2-diols to a-hydroxy acids in a cat. TEMPO/cat. NaOCl/NaClO2 system has been achieved. The use of a two-phase condition consisting of hydrophobic toluene and water suppresses the concomitant oxidative cleavage. A study of the mechanism suggests that the observed selectivity is derived from the precise solubility: control of diols and hydroxy acids as well as the active species Of TEMPO, Although the oxoammonium species TEMPO+Cl- is hydrophilic, the active species dissolves into the organic layer by the formation of the charge-transfer (CT) complex TEMPO-ClO2 under the reaction conditions.
• US6713472B1
  申请人：——

  公开号：US6713472B1

  公开（公告）日：2004-03-30
• US6960575B2
  申请人：——

  公开号：US6960575B2

  公开（公告）日：2005-11-01