(1R,2R)-2-amino-(N-benzyloxycarbonyl)-1-phenylpropane-1,3-diol | 285567-86-4

• 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: (1R,2R)-2-amino-(N-benzyloxycarbonyl)-1-phenylpropane-1,3-diol
• 英文别名: benzyl N-[(1R,2R)-1,3-dihydroxy-1-phenylpropan-2-yl]carbamate
• CAS: 285567-86-4
• 化学式: C₁₇H₁₉NO₄
• 分子量: 301.342
• InChiKey: ICKMPMAGRYUKNA-HZPDHXFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  78.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,2R)-2-amino-(N-benzyloxycarbonyl)-1-phenylpropane-1,3-diol 在 氢气 作用下， 生成 (1R,2R)-(-)-2-氨基-1-苯基-1,3-丙二醇
  参考文献：
  名称：

  Synthesis and biological evaluation of four stereoisomers of PDMP-analogue, N-(2-decylamino-3-hydroxy-3-phenylprop-1-yl)-β-valienamine, and related compounds

  摘要：

  All stereoisomers with regard to C-1 and 2 of 1-phenyl-2-decanoylamino-3-morpholino-1-propanol (PDMP) analogue containing unsaturated (beta-valienamine) and saturated 5a-carba-beta-D-glucopyranosylamine (beta-validamine) residues in place of morpholine moiety were synthesized. Although PDMP is a potent and specific glucosylceramide synthase inhibitor, the former valienamine analogues (4a-d) have been shown to be strong glucocerebrosidase inhibitors (IC50 3-7 x 10(-7) M). The latter validamine analogues (5a-d) were also moderate glucocerebrosidase inhibitors (IC50 5-20 x 10(-6) M). A series of compounds synthesized lacked an inhibitory potency against the glucosyltransferase at all. Whereas the analogue 6a composed of epimeric alpha-valienamine residue did not possess any potency against both enzymes. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00341-7
• 作为产物：
  描述：

  (1R,2R)-(-)-2-氨基-1-苯基-1,3-丙二醇 、 氯甲酸苄酯 在 sodium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 2.0h， 以99%的产率得到(1R,2R)-2-amino-(N-benzyloxycarbonyl)-1-phenylpropane-1,3-diol
  参考文献：
  名称：

  Syntheses of 1,2-Amino Alcohols and Their Applications for Oxazaborolidine Catalyzed Enantioselective Reduction of Aromatic Ketones

  摘要：

  从 (1R,2R)-2-氨基-1-苯基丙烷-1,3-二醇出发，合成了六种新的手性 1,2 氨基醇衍生物。用这些氨基醇衍生物和 BH3-Me2S 原位生成的噁唑硼烷对芳基酮进行不对称还原，得到了具有良好收率和中高对映体过量的仲醇。

  DOI：

  10.1071/ch06412

文献信息

• METHODS OF USING AS ANALGESICS 1-BENZYL-1-HYDROXY-2,3-DIAMINO-PROPYL AMINES, 3-BENZYL-3-HYDROXY-2-AMINO-PROPIONIC ACID AMIDES AND RELATED COMPOUNDS
  申请人：Leblond Bertrand

  公开号：US20090088433A1

  公开（公告）日：2009-04-02

  The compounds shown by the structural formulas below have analgesic effect and are used in compositions and methods for treating mammal in need of such treatment.

  下面结构式所示的化合物具有镇痛作用，用于治疗需要此类治疗的哺乳动物的组合物和方法中。
• METHODS FOR TREATING COGNITIVE DISORDERS USING 1-BENZYL-1-HYDROXY-2,3-DIAMINO-PROPYL AMINES, 3-BENZYL-3-HYDROXY-2-AMINO-PROPIONIC ACID AMIDES AND RELATED COMPOUNDS
  申请人：Donello John E.

  公开号：US20100190792A1

  公开（公告）日：2010-07-29

  Disclosed herein are methods of treating a patient suffering from a cognitive disorder using the following compounds (I, II, III, IV, V, VI, VII, VIII, IX, X, XI, XII, XIII).

  本文披露了使用以下化合物（I、II、III、IV、V、VI、VII、VIII、IX、X、XI、XII、XIII）治疗患有认知障碍的患者的方法。
• METHODS FOR TREATING COGNITIVE DISORDERS USING 1-ARYL-1-HYDROXY-2,3-DIAMINO-PROPYL AMINES, 1-HETEROARYL-1-HYDROXY-2,3-DIAMINO-PROPYL AMINES AND RELATED COMPOUNDS
  申请人：Donello John E.

  公开号：US20100105687A1

  公开（公告）日：2010-04-29

  Disclosed herein are methods of treating a patient suffering from a cognitive disorder using compounds of the following formula, Formula (2), wherein the variables have the meaning defined in the specification.

  本文披露了使用以下公式（2）的化合物治疗患有认知障碍的患者的方法，其中变量的含义在说明书中定义。
• 1-ARYL-1-HYDROXY-2,3-DIAMINO-PROPYL AMINES, 1-HETEROARYL-1-HYDROXY-2,3-DIAMINO-PROPYL AMINES AND RELATED COMPOUNDS HAVING ANALGESIC AND/OR IMMUNO STIMULANT ACTIVITY
  申请人：Leblond Bertrand

  公开号：US20110288094A1

  公开（公告）日：2011-11-24

  Compounds of the formula where the variables have the meaning defined in the specification have analgesic and/or immunostimulant effect in mammals.

  式中变量的含义如规范所定义，该化合物在哺乳动物中具有镇痛和/或免疫刺激作用。
• METHODS OF USING AS ANALGESICS 1-BENZYL-1-HYDROXY-2, 3-DIAMINO-PROPYL AMINES, 3-BENZYL-3-HYRDROXY-2-AMINO-PROPIONIC ACID AMIDES AND RELATED COMPOUNDS
  申请人：Leblond Bertrand

  公开号：US20120225881A1

  公开（公告）日：2012-09-06

  The compounds shown by the structural formulas below have analgesic effect and are used in compositions and methods for treating mammal in need of such treatment.

  以下结构式所示的化合物具有镇痛作用，并用于治疗需要此类治疗的哺乳动物的组合物和方法。