(R)-methyl 2-((tert-butoxycarbonyl)amino)-3-(tosyloxy)propanoate | 126645-21-4

• 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: (R)-methyl 2-((tert-butoxycarbonyl)amino)-3-(tosyloxy)propanoate
• 英文别名: methyl N-(tert-butoxycarbonyl)-O-[(4-methylphenyl)sulfonyl]-D-serinate；N-(tert-butoxycarbonyl)-O-[(4-methylphenyl)sulfonyl]-D-serine methyl ester；Methyl N-(tert-butoxycarbonyl)-O-tosyl-D-serinate；methyl (2R)-3-(4-methylphenyl)sulfonyloxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
• CAS: 126645-21-4
• 化学式: C₁₆H₂₃NO₇S
• 分子量: 373.427
• InChiKey: VVBLIPVUGGNLGW-CYBMUJFWSA-N

物化性质

• 沸点：
  520.0±50.0 °C(Predicted)
• 密度：
  1.236±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  116
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (R)-methyl 2-((tert-butoxycarbonyl)amino)-3-(tosyloxy)propanoate 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 生成 3-叠氮-N-BOC-D-丙氨酸甲酯,3-AZIDO-N-BOC-D-ALANINEMETHYLESTER
  参考文献：
  名称：

  一种新型含根瘤菌素样三唑氨基酸的合成

  摘要：

  描述了从丝氨酸合成根唑菌素的新 1,2,3-三唑类似物的四种立体异构体。关键步骤是在乙炔基甘氨酸合成子上进行 Huisgen 1,3-偶极环加成。

  DOI：

  10.1055/s-0036-1588300
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 吡啶 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 16.33h， 生成 (R)-methyl 2-((tert-butoxycarbonyl)amino)-3-(tosyloxy)propanoate
  参考文献：
  名称：

  A Novel Agonist of the Type 1 Lysophosphatidic Acid Receptor (LPA₁), UCM-05194, Shows Efficacy in Neuropathic Pain Amelioration

  摘要：

  Neuropathic pain (NP) is a complex chronic pain state with a prevalence of almost 10% in the general population. Pharmacological options for NP are limited and weakly effective, so there is a need to develop more efficacious NP attenuating drugs. Activation of the type 1 lysophosphatidic acid (LPA(1)) receptor is a crucial factor in the initiation of NP. Hence, it is conceivable that a functional antagonism strategy could lead to NP mitigation. Here we describe a new series of LPA(1) agonists among which derivative (S)-17 (UCM-05194) stands out as the most potent and selective LPA(1) receptor agonist described so far (E-max = 118%, EC50 = 0.24 mu M, KD = 19.6 nM; inactive at autotaxin and LPA(2-6) receptors). This compound induces characteristic LPA(1)-mediated cellular effects and prompts the internalization of the receptor leading to its functional inactivation in primary sensory neurons and to an efficacious attenuation of the pain perception in an in vivo model of NP.

  DOI：

  10.1021/acs.jmedchem.9b01287

文献信息

• Imidazole derivative, process for producing the same, and use
  申请人：Kubo Keiji

  公开号：US20070004736A1

  公开（公告）日：2007-01-04

  There is provided an imidazole derivative useful as a thrombosis treating agent, which is represented by the formula (I): wherein R represents an optionally substituted cyclic hydrocarbon group or an optionally substituted heterocyclic group, W represents a bond or an optionally substituted divalent linear hydrocarbon group, X represents an optionally substituted divalent hydrocarbon group, Y represents —CO—, —S(O)—, —S(O) 2 — or a bond, ring A represents an optionally substituted pyrrolidine ring, an optionally substituted piperidine ring or an optionally substituted perhydroazepine ring, Z 1 and Z 3 independently represent a bond or an optionally substituted divalent linear hydrocarbon group, Z 2 represents —N(R 1 )—, —O—, —S(O)—, —S(O) 2 —, —CO—, —CH(R 1 )— or a bond, ring B represents an optionally substituted imidazole ring, wherein a substituent which the optionally substituted imidazole ring represented by ring B may have may be taken together with R 1 to form an optionally substituted ring, and a represents 0, 1 or 2.

  提供了一种咪唑衍生物，用作治疗血栓的药物，其化学式表示为(I)式：其中R代表可选取代的环烃基或可选取代的杂环基，W代表键或可选取代的二价直链烃基，X代表可选取代的二价烃基，Y代表-CO-、-S(O)-、-S(O)2-或键，环A代表可选取代的吡咯烷环、可选取代的哌啶环或可选取代的过氢杂环己烷环，Z1和Z3独立地代表键或可选取代的二价直链烃基，Z2代表-N(R1)-、-O-、-S(O)-、-S(O)2-、-CO-、-CH(R1)-或键，环B代表可选取代的咪唑环，其中可选取代的咪唑环所具有的取代基可以与R1一起形成可选取代的环，a代表0、1或2。
• IMIDAZOLE DERIVATIVE, THEIR PRODUCTION AND USE
  申请人：KUBO Keiji

  公开号：US20110009389A1

  公开（公告）日：2011-01-13

  There is provided an imidazole derivative useful as a thrombosis treating agent, which is represented by the formula (I): wherein R represents an optionally substituted cyclic hydrocarbon group or an optionally substituted heterocyclic group, W represents a bond or an optionally substituted divalent linear hydrocarbon group, X represents an optionally substituted divalent hydrocarbon group, Y represents —CO—, —S(O)—, —S(O) 2 — or a bond, ring A represents an optionally substituted pyrrolidine ring, an optionally substituted piperidine ring or an optionally substituted perhydroazepine ring, Z 1 and Z 3 independently represent a bond or an optionally substituted divalent linear hydrocarbon group, Z 2 represents —N(R 1 )—, —O—, —S(O)—, —S(O) 2 —, —CO—, —CH(R 1 )— or a bond, ring B represents an optionally substituted imidazole ring, wherein a substituent which the optionally substituted imidazole ring represented by ring B may have may be taken together with R 1 to form an optionally substituted ring, and a represents 0, 1 or 2.

  提供了一种咪唑衍生物，可用作治疗血栓的药物，其化学式表示为（I）：其中R代表可选取代的环烃基或可选取代的杂环基，W代表键或可选取代的二价线性烃基，X代表可选取代的二价烃基，Y代表-CO-，-S（O）-，-S（O）2-或键，环A代表可选取代的吡咯烷环，可选取代的哌啶环或可选取代的过氢化脂肪环，Z1和Z3独立地代表键或可选取代的二价线性烃基，Z2代表-N（R1）-，-O-，-S（O）-，-S（O）2-，-CO-，-CH（R1）-或键，环B代表可选取代的咪唑环，其中可选取代的咪唑环所代表的取代基可以与R1一起形成可选取代的环，a代表0，1或2。
• IMIDAZOLE DERIVATIVE, PROCESS FOR PRODUCING THE SAME, AND USE
  申请人：Takeda Pharmaceutical Company Limited

  公开号：EP1564213A1

  公开（公告）日：2005-08-17

  There is provided an imidazole derivative useful as a thrombosis treating agent, which is represented by the formula (I): wherein R represents an optionally substituted cyclic hydrocarbon group or an optionally substituted heterocyclic group, W represents a bond or an optionally substituted divalent linear hydrocarbon group, X represents an optionally substituted divalent hydrocarbon group, Y represents -CO-, -S(O)-, -S(O)2- or a bond, ring A represents an optionally substituted pyrrolidine ring, an optionally substituted piperidine ring or an optionally substituted perhydroazepine ring, Z1 and Z3 independently represent a bond or an optionally substituted divalent linear hydrocarbon group, Z2 represents -N(R1)-, -O-, - S(O)-, -S(O)2-, -CO-, -CH(R1)- or a bond, ring B represents an optionally substituted imidazole ring, wherein a substituent which the optionally substituted imidazole ring represented by ring B may have may be taken together with R1 to form an optionally substituted ring, and a represents 0, 1 or 2.

  提供了一种咪唑衍生物，可用作血栓治疗剂，其由式(I)表示： 其中 R 代表任选取代的环状烃基或任选取代的杂环基，W 代表键或任选取代的二价线性烃基，X 代表任选取代的二价烃基，Y 代表 -CO-、-S(O)-、-S(O)2- 或键，环 A 代表任选取代的吡咯烷环、任选取代的哌啶环或任选取代的全氢氮杂卓环、Z1 和 Z3 独立地代表键或任选取代的二价线性烃基，Z2 代表-N(R1)-、-O-、-S(O)-、-S(O)2-、-CO-、-CH(R1)- 或键，环 B 代表任选取代的咪唑环，其中环 B 所代表的任选取代的咪唑环可能具有的取代基可与 R1 一起形成任选取代的环，a 代表 0、1 或 2。
• EP1564213
  申请人：——

  公开号：——

  公开（公告）日：——
• Intramolecular Pictet-Spengler reaction of N-alkoxytryptamines. 3. Stereoselective synthesis of (-)-debromoeudistomin L and (-)-O-methyldebromoeudistomin E and their stereoisomers
  作者：Pedro H. H. Hermkens、Jan H. Van Maarseveen、Harry C. J. Ottenheijm、Chris G. Kruse、Hans W. Scheeren

  DOI：10.1021/jo00300a011

  日期：1990.6