methyl N-tert-butoxycarbonyl-4-{[(trifluoromethyl)sulfonyl]oxy}-D-phenylglycinate | 313490-19-6

• 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: methyl N-tert-butoxycarbonyl-4-{[(trifluoromethyl)sulfonyl]oxy}-D-phenylglycinate
• 英文别名: methyl(2R)-[(tert-butoxycarbonyl)amino]{4{{(trifluoromethyl)sulfonyl}oxy}phenyl}acetate；methyl (2R)-2-{[(tert-butoxy)carbonyl]amino}-2-{4-[(trifluoromethane)sulfonyloxy]phenyl}acetate；methyl (2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-2-[4-(trifluoromethylsulfonyloxy)phenyl]acetate
• CAS: 313490-19-6
• 化学式: C₁₅H₁₈F₃NO₇S
• 分子量: 413.372
• InChiKey: RCWXVVSPWNKHBK-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  116
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  methyl N-tert-butoxycarbonyl-4-{[(trifluoromethyl)sulfonyl]oxy}-D-phenylglycinate 在 sodium tetrahydroborate 、 盐酸 、 水 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 (R)-4-(1-((tert-butoxycarbonyl)amino)-2-hydroxyethyl)phenyl trifluoromethanesulfonate
  参考文献：
  名称：

  Substituted bis-amide metalloprotease inhibitors

  摘要：

  这项发明涉及Formula (I)的取代双酰胺嘧啶化合物，这些化合物对于治疗金属蛋白酶介导的疾病，特别是MMP-13相关疾病是有用的。

  公开号：

  US20070155739A1
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 sodium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 二氯甲烷 为溶剂， 生成 methyl N-tert-butoxycarbonyl-4-{[(trifluoromethyl)sulfonyl]oxy}-D-phenylglycinate
  参考文献：
  名称：

  Suppression of racemization in the carbonylation of amino acid-derived aryl triflates

  摘要：

  The carbonylation of enantiopure phenylglycine-derived aryl triflates was achieved to afford 4-carboxyphenylglycine analogs with high enantiomeric excesses (88 to >99% ee). Amide analogs of phenylglycine were well-tolerated in the hydroxy- and methoxycarbonylation processes, providing efficient access to benzoic acid and ester building blocks. The % ee of the product was dependent on the relative steric bulk of both the amino acid substrate and the requisite amine base, with (Pr2NEt)-Pr-i proving optimal in minimizing product racemization. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.04.145

文献信息

• Derivatives of Dihydroxypyrrolidine as Anti-Cancer Compounds
  申请人：EPFL Ecole Polytechnique Fédérale de Lausanne

  公开号：EP2067771A1

  公开（公告）日：2009-06-10

  The present invention relates to derivatives of dihydroxypyrrolidine useful in the treatment of cancer. The invention further relates to a process for making the compounds. The compounds are inhibitors of α mannosidase, and possibly, also inhibit nicotinamide phosphoribosyl transferase.

  本发明涉及一种二羟基吡咯烷衍生物，可用于癌症治疗。该发明还涉及一种制备该化合物的方法。该化合物是α甘露糖苷酶的抑制剂，可能也抑制烟酰胺磷酸核糖转移酶。
• Novel 2-[(benzylamino)methyl]pyrrolidine-3,4-diol derivatives as α-mannosidase inhibitors and with antitumor activities against hematological and solid malignancies
  作者：Claudia Bello、Michele Cea、Giovanna Dal Bello、Anna Garuti、Ilaria Rocco、Gabriella Cirmena、Eva Moran、Aimable Nahimana、Michel A. Duchosal、Floriana Fruscione、Paolo Pronzato、Francesco Grossi、Franco Patrone、Alberto Ballestrero、Marc Dupuis、Bernard Sordat、Alessio Nencioni、Pierre Vogel

  DOI：10.1016/j.bmc.2010.03.009

  日期：2010.5

  Novel alpha-mannosidase inhibitors of the type (2R,3R,4S)-2-([(1R)-2- hydroxy-1-arylethyl]amine}methyl) pyrrolidine-3,4-diol have been prepared and assayed for their anticancer activities. Compound 30 with the aryl group = 4-trifluoromethylbiphenyl inhibits the proliferation of primary cells and cell lines of different origins, irrespective of Bcl-2 expression levels, inducing a G2/Mcell cycle arrest and by modification of genes involved in cell cycle progression and survival. (C) 2010 Elsevier Ltd. All rights reserved.
• [EN] SUBSTITUTED BIS-AMIDE METALLOPROTEASE INHIBITORS<br/>[FR] INHIBITEURS DE MÉTALLOPROTÉASES À BASE DE BISAMIDES SUBSTITUÉS
  申请人：ALANTOS PHARMACEUTICALS INC

  公开号：WO2007079199A2

  公开（公告）日：2007-07-12

  [EN] This invention relates to substituted bis-amide pyrimidine compounds of Formula (I), which are useful for the treatment of metalloprotease mediated diseases, in particular MMP-13 related diseases.
  [FR] La présente invention concerne des composés de bis-amidopyrimidine substitués de formule (I), qui sont utiles pour le traitement de maladies à médiation par une métalloprotéase, en particulier les maladies liées à la MMP-13.