benzyl 2(S)-<(tert-butoxycarbonyl)amino>-3-(4'-nitrophenyl)propionate | 127977-25-7

• 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: benzyl 2(S)-<(tert-butoxycarbonyl)amino>-3-(4'-nitrophenyl)propionate
• 英文别名: N-tert-butyloxycarbonyl-p-nitro-L-phenylalanine benzyl ester；benzyl 2(S)-[(tert-butoxycarbonyl)amino]-3-(4'-nitrophenyl)propionate；benzyl (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-(4-nitrophenyl)propanoate
• CAS: 127977-25-7
• 化学式: C₂₁H₂₄N₂O₆
• 分子量: 400.431
• InChiKey: WGNWCTLYGQSORT-SFHVURJKSA-N

物化性质

• 沸点：
  560.1±50.0 °C(Predicted)
• 密度：
  1.226±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  benzyl 2(S)-<(tert-butoxycarbonyl)amino>-3-(4'-nitrophenyl)propionate 在 palladium on activated charcoal 盐酸 、 氯化亚砜 、 氢气 、 甲烷 、 一水合肼 作用下， 以 1,4-二氧六环 、 甲醇 、 氯仿 、 水 、 溶剂黄146 为溶剂， 反应 31.0h， 生成 L-prolylmelphalan
  参考文献：
  名称：

  Synthesis of ?-aminoacyl derivatives of melphalan for use in antibody directed enzyme pro-drug therapy

  摘要：

  L-Alanyl-, D-alanyl-, L-prolyl-, L-pyroglutamyl- and D-phenylalanylmelphalan were synthesized in 8 steps, with the reactive nitrogen mustard moiety formed at the penultimate step. After protection of p-nitrophenylalanine with benzyl ester and N-t-butyloxycarbonyl (BOC) groups, the aromatic nitro was reduced to an amine which was reacted with ethylene oxide to give a product with a bis(2-hydroxyethyl)amino moiety. After removal of BOC, it was coupled to the relevant N-benzyloxycarbonyl-alpha-amino acid. Chlorination of hydroxyethyl yielded the bis(2-chlorethyl)amino compound. Final removal of protecting groups was by catalytic hydrogenolysis. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01139-9
• 作为产物：
  描述：

  BOC-L-丝氨酸苄酯对甲苯磺酸酯 在 bis(tri-o-tolylphosphine)palladium trichloride 锌铜偶 、 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 25.5h， 生成 benzyl 2(S)-<(tert-butoxycarbonyl)amino>-3-(4'-nitrophenyl)propionate
  参考文献：
  名称：

  Preparation of enantiomerically pure protected 4-oxo .alpha.-amino acids and 3-aryl .alpha.-amino acids from serine

  摘要：

  The organozinc reagent 13, prepared from the protected beta-iodo alanine derivative 3c using ultrasonic activation, is efficiently acylated using acid chlorides in the presence of bis(triphenylphosphine)palladium dichloride to give enantiomerically pure protected 4-oxo-alpha-amino acids 17 in 39-90% yield (13 examples). Zinc reagent 13 can also be coupled with aryl iodides in the presence of bis(tri-o-tolylphosphine)palladium dichloride to give enantiomerically pure protected phenylalanine analogues 26, 29, and 30 in 10-67% yield (11 examples). The reaction tolerates the presence of a variety of functional groups in the acid chloride and the aryl iodide and provides derivatives which can be easily deprotected, at either the carboxyl or amino terminus, to give intermediates suitable for peptide synthesis.

  DOI：

  10.1021/jo00038a030

文献信息

• Benzothiazole benzimidazole (S)-isothiazolidinone derivatives as protein tyrosine phosphatase-1B inhibitors
  作者：Richard B. Sparks、Padmaja Polam、Wenyu Zhu、Matthew L. Crawley、Amy Takvorian、Erin McLaughlin、Min Wei、Paul J. Ala、Lucie Gonneville、Nancy Taylor、Yanlong Li、Richard Wynn、Timothy C. Burn、Phillip C.C. Liu、Andrew P. Combs

  DOI：10.1016/j.bmcl.2006.10.079

  日期：2007.2

  demonstrated that the benzothiazole benzimidazole forms bi-dentate H-bonds to Asp48, and the benzothiazole interacts with the surface of the protein in a solvent exposed region towards the C-site. The design, synthesis, and SAR of this novel series of benzothiazole benzimidazole containing (S)-IZD inhibitors of PTP1B are presented herein.

  通过三肽（S）-IZD蛋白酪氨酸磷酸酶1B（PTP1B）抑制剂1的拟肽修饰，发现了苯并噻唑苯并咪唑（S）-异噻唑烷酮（（S）-IZD）衍生物5。这些衍生物是有效，竞争和可逆的抑制剂。具有改善的caco-2渗透性的PTP1B的制备。抑制剂5 / PTP1B在2.2A分辨率下的X射线共晶体结构表明，苯并噻唑苯并咪唑与Asp48形成双齿H键，并且苯并噻唑在溶剂暴露区域向C处与蛋白质表面相互作用。 -地点。本文介绍了该新型系列的含PTP1B的（S）-IZD抑制剂的苯并噻唑苯并咪唑的设计，合成和SAR。
• Synthesis of N-α-aminoacyl derivatives of melphalan for potential use in drug targeting
  作者：Dale W. Larden、H.T.Andrew Cheung

  DOI：10.1016/0040-4039(96)01665-6

  日期：1996.10

  N-L- and D-alanyl derivatives (9a, 9b) of melphalan (1) have been synthesized in eight steps (9a, 22%; 9b, 18% overall yield) from p-nitro-L-phenylalanine.

  从对-硝基-L-苯丙氨酸以八步（9a，22％；9b，总收率18％）合成了melphalan（1）的NL-和D-丙氨酰基衍生物（9a，9b）。
• Synthesis of enantiomerically pure protected β-aryl alanines
  作者：Richard F.W. Jackson、Martin J. Wythes、Anthony Wood

  DOI：10.1016/s0040-4039(01)93511-7

  日期：1989.1