(S)-5-(4-methylphenylsulfonyloxymethyl)-1,3-oxazolidin-2-one | 109794-68-5

• 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: (S)-5-(4-methylphenylsulfonyloxymethyl)-1,3-oxazolidin-2-one
• 英文别名: (S)-5-tosyloxymethyl-1,3-oxazolidine-2-one；[(5S)-2-oxo-1,3-oxazolidin-5-yl]methyl 4-methylbenzenesulfonate
• CAS: 109794-68-5
• 化学式: C₁₁H₁₃NO₅S
• 分子量: 271.294
• InChiKey: OCDQYYSOGFFJPA-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  90.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-苯基-2-丙烯酰氯 、 (S)-5-(4-methylphenylsulfonyloxymethyl)-1,3-oxazolidin-2-one 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 25.25h， 生成 (S)-(3-cinnamoyl-2-oxo-1,3-oxazolidin-5-yl)methyl 4-methylbenzenesulfonate
  参考文献：
  名称：

  Synthesis and antibacterial evaluation of oxazolidin-2-ones structurally related to linezolid

  摘要：

  Compounds structurally related to the known antimicrobial drug linezolid were selected in order to evaluate the influence of electron-withdrawing properties and altered geometric features as a result of the N-substituent modification. After a preliminary study of molecular modeling, cinnamoyl-, pyridin- and pyrimidinoxazolidin-2-ones were synthesized. None of the new compounds showed antibacterial activity.

  DOI：

  10.1016/j.farmac.2004.05.002
• 作为产物：
  描述：

  (5S)-5-(羟甲基)-1,3-恶唑烷-2-酮 、 对甲苯磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以59%的产率得到(S)-5-(4-methylphenylsulfonyloxymethyl)-1,3-oxazolidin-2-one
  参考文献：
  名称：

  吲哚酰胺对3-磷酸甘油酸脱氢酶（PHGDH）的抑制消除了癌细胞中新丝氨酸的合成。

  摘要：

  癌细胞会重新编程其新陈代谢，以支持生长并缓解细胞应激。丝氨酸合成途径已被鉴定为在癌症中经常改变的代谢途径，并且开发靶向此途径的药理学已引起相当大的兴趣。在这里，我们报道了一系列抑制人类3-磷酸甘油酸脱氢酶（PHGDH）的吲哚酰胺，该酶催化丝氨酸合成途径的第一步。使用X射线晶体学，我们显示吲哚酰胺结合PHGDH的NAD +口袋。通过基于结构的优化，我们能够在酶促IC 50分析中开发出对PHGDH具有低纳摩尔亲和力的化合物。在细胞分析中，最有效的化合物从头开始抑制具有低微摩尔至亚微摩尔活性的丝氨酸合成，并且这些化合物成功消除了在无丝氨酸培养基中癌细胞的增殖。此处报道的吲哚酰胺系列代表了对先前发表的PHGDH抑制剂的重要改进，因为它们的效力更强，其作用机理也得到了更好的定义。

  DOI：

  10.1016/j.bmcl.2019.07.011

文献信息

• Enantioconvergent chemoenzymatic synthesis of (R)-gamma-amino-beta-hydroxybutyric acid ((R)-GABOB)
  申请人：Kamal Ahmed

  公开号：US20060141606A1

  公开（公告）日：2006-06-29

  The present invention particularly relates to a chemoenzymatic process for the stereoselective preparation of both enantiomers of 3-hydroxy-4-trityloxy butanenitrile key intermediates for the preparation of (R)-GABOB by lipase mediated kinetic resolution of its racemates and their effective application in the enantioconvergent synthesis of (R)-GABOB.

  本发明特别涉及一种化学酶法过程，用于立体选择性制备3-羟基-4-三苄氧基丁腈的两个对映体，该中间体是通过脂肪酶介导的拆分其外消旋体制备(R)-GABOB的关键中间体，并且有效地应用于(R)-GABOB的对映体转化合成中。
• Enantioconvergent chemoenzymatic synthesis of (R)-γ-amino-β-hydroxybutyric acid ((R)-GABOB)
  申请人：Council of Scientific and Industrial Research

  公开号：US07374926B2

  公开（公告）日：2008-05-20

  The present invention particularly relates to a chemoenzymatic process for the stereoselective preparation of both enantiomers of 3-hydroxy-4-trityloxy butanenitrile key intermediates for the preparation of (R)-GABOB by lipase mediated kinetic resolution of its racemates and their effective application in the enantioconvergent synthesis of (R)-GABOB.

  本发明特别涉及一种化酶过程，用于立体选择性制备3-羟基-4-三苄氧基丁腈的两个对映体，该中间体是通过脂肪酶介导的其外消旋体的动力学分辨制备(R)-GABOB的制备的关键中间体，并且它们在(R)-GABOB的对映体转化合成中的有效应用。
• New chemoenzymatic pathway for β-adrenergic blocking agents
  作者：Ahmed Kamal、G.B. Ramesh Khanna、T. Krishnaji、Venkatesh Tekumalla、R. Ramu

  DOI：10.1016/j.tetasy.2005.02.015

  日期：2005.4

  The lipase mediated kinetic resolution of pharmaceutically important beta-hydroxy nitrites is described in high enantionteric excesses and good yields. Some of the chiral beta-hydroxy nitriles have been employed in the synthesis of P-adrenergic blocking agents such as propranolol, alprenolol and moprolol. This protocol has also been extended for the enantiopure preparation of 5-(4-tosyloxymethyl)-1,3-oxazolidine-2-one and 3-liydroxy-4-tosyloxybutaiieiiitrile, chiral intermediates of high synthetic value. (c) 2005 Elsevier Ltd. All rights reserved.
• Lipase-mediated resolution of 3-hydroxy-4-trityloxybutanenitrile: synthesis of 2-amino alcohols, oxazolidinones and GABOB
  作者：Ahmed Kamal、G.B. Ramesh Khanna、T. Krishnaji、R. Ramu

  DOI：10.1016/j.tetasy.2006.04.019

  日期：2006.4

  Lipase-mediated kinetic resolution of 3-hydroxy-4-trityloxybutanenitrile gave the (S)-alcohol and (R)-acetate in good yields and high enantioselectivities. The resolution using Pseudomonas cepacia lipase (Burkholderia cepacia) immobilized on modified ceramic particles (PS-C) in diisopropyl ether gave the best results. The use of base additives in this transesterification drastically reduces the reaction time without effecting the yields or enantioselectivities. Resolved 3-hydroxy-4-trityloxybutanenitrile has been utilized for the synthesis of enantiomerically pure 5-tosyloxymethyl-1,3-oxazolidine-2-one, which is an important intermediate for the preparation of beta-adrenergic blocking agents and oxazolidinone based antimicrobial agents. Enantiomerically pure (R)-3-hydroxy-4-trityloxybutanenitrile and (S)-5-tosyloxymethyl-1,3-oxazolidine-2-one have been utilized in the enantioconvergent synthesis of (R)-GABOB. (c) 2006 Published by Elsevier Ltd.
• From carnitinamide to 5-aminomethyl-2-oxazolidinones
  作者：Cristiano Bolchi、Marco Pallavicini、Matteo Binda、Laura Fumagalli、Ermanno Valoti

  DOI：10.1016/j.tetasy.2012.02.006

  日期：2012.2

  Carnitinamide chloride, an immediate synthetic precursor of carnitine, was chlorinated at the amide nitrogen. The resultant carnitinechloramide chloride, when treated with a base, revealed that the first-formed isolable and characterisable carnitinechloramide inner salt undergoes solid state conversion into 5-trimethylammoniomethyl-2-oxazolidinone chloride via Hoffmann rearrangement and intramolecular cyclization of the beta-hydroxyisocyanate. The trimethylaminomethyl substituent at C-5 of the 2-oxazolidinone was converted into a dimethylaminomethyl group by microwave-assisted demethylation in DMF and then into a methylaminomethyl group by decomposition of the alpha-chloroethyl carbamate obtained by treatment with alpha-chloroethyl chloroformate. This sequence of reactions was then applied to both (S)- and (R)-carnitinamide chloride without any racemization to yield both enantiomers of 5-aminomethyl-2-oxazolidinones that are mono-, di- and tri-methylated at the exocyclic nitrogen. (C) 2012 Elsevier Ltd. All rights reserved.