O-[(4-甲基苯基)磺酰基]-N-[苄氧羰基]-L-丝氨酸甲酯 | 1492-52-0

• 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
• 中文名称: O-[(4-甲基苯基)磺酰基]-N-[苄氧羰基]-L-丝氨酸甲酯
• 中文别名: 苄氧羰基-O-对甲苯磺酰-L-丝氨酸甲酯
• 英文名称: methyl (S)-2-(benzyloxycarbonlamino)-3-(p-toluenesulfonyl)propionate
• 英文别名: N-benzyloxycarbonyl-O-tosyl-L-serine methyl ester；N-benzyloxycarbonyl-O-p-toluenesulfonyl-L-serine methyl ester；N-Carbobenzoxy-O-tosyl-L-serinmethylester；Z-Ser(Tos)-Ome；methyl (2S)-3-(4-methylphenyl)sulfonyloxy-2-(phenylmethoxycarbonylamino)propanoate
• CAS: 1492-52-0
• 化学式: C₁₉H₂₁NO₇S
• 分子量: 407.444
• InChiKey: VHGXRGXCDVQIKS-KRWDZBQOSA-N

物化性质

• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  116
• 氢给体数：
  1
• 氢受体数：
  7

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  存于2-8°C环境中，需密闭保存并在干燥条件下存放。

制备方法与用途

Z-Ser(Tos)-OMe是一种丝氨酸衍生物[1]。

反应信息

• 作为反应物：
  描述：

  O-[(4-甲基苯基)磺酰基]-N-[苄氧羰基]-L-丝氨酸甲酯 在 benzyltriethylammonium tetrathiomolybdate 作用下， 以 乙腈 为溶剂， 以78%的产率得到N,N'-bis[(phenylmethoxy)carbonyl]-L-cystine 1,1'-dimethyl ester
  参考文献：
  名称：

  Utility of tetrathiomolybdate and tetraselenotungstate: efficient synthesis of cystine, selenocystine, and their higher homologues

  摘要：

  Efficient synthesis of cystine, selenocystine, and their higher homologues like homo and bishomo amino acid derivatives from natural amino acid derivatives using tetrathiomolybdate and tetraselenotungstate reagents under mild and neutral conditions is reported. The generality of the reaction has been studied by capping various groups to amino and carboxyl components of canonical amino acids. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01222-x
• 作为产物：
  描述：

  N-苄氧羰基-L-丝氨酸 在 氯化亚砜 作用下， 以 吡啶 为溶剂， 生成 O-[(4-甲基苯基)磺酰基]-N-[苄氧羰基]-L-丝氨酸甲酯
  参考文献：
  名称：

  Utility of tetrathiomolybdate and tetraselenotungstate: efficient synthesis of cystine, selenocystine, and their higher homologues

  摘要：

  Efficient synthesis of cystine, selenocystine, and their higher homologues like homo and bishomo amino acid derivatives from natural amino acid derivatives using tetrathiomolybdate and tetraselenotungstate reagents under mild and neutral conditions is reported. The generality of the reaction has been studied by capping various groups to amino and carboxyl components of canonical amino acids. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01222-x

文献信息

• Coordination chemistry of phosphanyl amino acids: solid state and solution structures of neutral and cationic rhodium complexes
  作者：Christian Meyer、Markus Scherer、Hartmut Schönberg、Heinz Rüegger、Sandra Loss、Volker Gramlich、Hansjörg Grützmacher

  DOI：10.1039/b512653c

  日期：——

  and [RhCl(cod)(ZSerArs)] 11 which were characterized by X-ray diffraction studies. A common structural feature is an intramolecular (N)H⋯Cl(Rh)-hydrogen bridge which according to NMR investigations remains intact in solution. The abstraction of chloride from the coordination sphere of Rh(I) in 8 or 10 has a profound structural impact. While in 8 and 10, the ligands bind in a monodentate fashion, via

  磷化铜或砷化物络合物[Cu（EPh 2）（neo）]（E = P，As，neo = 2,9-二甲基-1,10-菲咯啉；简称：neocuprine）与受N保护的溴化物选择性反应丝氨酸衍生物，2-（小号） - （烷氧基羰基）-3- bromomethylpropionates 1A-1C（ROCO SerBr，一个：R =的PhCH 2，b：TBU，Ç：ME），以得到相应的phOSa href=https://www.molaid.com/MS_15603 target="_blank">SPhanylated或arsanylated氨基酸，ROCO SerPhOS（3A-C：PHOS = PPH 2）和Ž SerArs 7（ARS = ASPH 2，Z =的PhCH 2 OCO）。这二肽 同样准备了Z AlaSerPhOS 3d。这膦类 3a–d和rs 7与[Rh 2（µ-Cl）2（cod）2 ]干净反应，得到铑（I）络合物[RhCl（cod）（Z SerPhOS）] 8，[RhCl（cod）（Boc
• Preparation of S-aryl-cysteine and its derivatives
  申请人：F. Hoffmann-La Roche AG

  公开号：US06229041B1

  公开（公告）日：2001-05-08

  The present invention provides a method for preparing S-aryl cysteine. Specifically, the present invention provides enantioselective method for preparing S-aryl cysteine starting from cystine, cysteine or serine amino acid. The methods of the present invention provides S-aryl cysteine in enantiomeric excess of greater than about 96%.

  本发明提供了一种制备S-芳基半胱氨酸的方法。具体地，本发明提供了一种选择性手性的方法，从半胱氨酸、半胱氨酸或丝氨酸氨基酸出发制备S-芳基半胱氨酸。本发明的方法提供了超过96%的对映体过量的S-芳基半胱氨酸。
• Glycogen Phosphorylase Inhibitor Compounds and Pharmaceutical Compositions Thereof
  申请人：Evans Karen

  公开号：US20070249670A1

  公开（公告）日：2007-10-25

  The invention relates to glycogen phosphorylase inhibitor compounds, pharmaceutical compositions of these compounds, methods of treatment using the pharmaceutical compositions to treat diabetes, conditions associated with diabetes, and/or tissue ischemia, including myocardial ischemia, and processes for making the compounds.

  本发明涉及糖原磷酸化酶抑制剂化合物、这些化合物的药物组合物、使用这些药物组合物治疗糖尿病、与糖尿病相关的疾病和/或组织缺血，包括心肌缺血的方法，以及制备这些化合物的过程。
• PROCESS FOR PRODUCING CYSTEINE DERIVATIVES
  申请人：KANEKA CORPORATION

  公开号：EP0897911A1

  公开（公告）日：1999-02-24

  This invention relates to a method comprising reacting an amino acid derivative of the following general formula (I): (wherein R1 represents an amino-protective group; R0 represents hydrogen or, taken together with R1, represents an amino-protecting group; R2 represents a carboxy-protecting group; X represents a leaving group) with a thiol compound of the following general formula (II):         R3SH     (II) (wherein R3 represents an alkyl group of 1 to 7 carbon atoms, an aryl group of 6 to 10 carbon atoms, or an aralkyl group of 7 to 10 carbon atoms) to give a cysteine derivative of the following general formula (III): (wherein R0, R1, R2, and R3 are as defined above), wherein the reaction is conducted in the presence of a base and water in an organic reaction solvent.

  本发明涉及一种方法，包括使以下通式(I)的氨基酸衍生物发生反应： (其中 R1 代表氨基保护基团；R0 代表氢或与 R1 一起代表氨基保护基团；R2 代表羧基保护基团；X 代表离去基团）与下 列通式（II）的硫醇化合物反应： R3SH (II) (其中 R3 代表 1 至 7 个碳原子的烷基、6 至 10 个碳原子的芳基或 7 至 10 个碳原子的芳烷基），得到下 列通式（III）的半胱氨酸衍生物： (其中 R0、R1、R2 和 R3 如上定义），其中反应在有机反应溶剂中，在碱和水存在下进行。
• Process for S-aryl-L-cysteine and derivatives
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP0968997A2

  公开（公告）日：2000-01-05

  The present invention provides methods for preparing S-aryl cysteines in enantiomeric excess of greater than about 96%. Specifically, the present invention provides enantioselective methods for preparing S-aryl cysteines starting from cystine, cysteine or a serine.

  本发明提供了制备对映体过量率大于约 96% 的 S-芳基半胱氨酸的方法。具体来说，本发明提供了从胱氨酸、半胱氨酸或丝氨酸开始制备 S-芳基半胱氨酸的对映体选择性方法。