N-Boc-(4S)-acetoxy proline methyl ester | 188109-82-2

• 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: N-Boc-(4S)-acetoxy proline methyl ester
• 英文别名: 1-(tert-butyl) 2-methyl (2S,4S)-4-acetoxypyrrolidine-1,2-dicarboxylate；(2S,4S)-1-tert-butyl 2-methyl 4-acetoxypyrrolidine-1,2-dicarboxylate；(2S,4S)-N-Boc-4-acetoxy-proline methyl ester；1-O-tert-butyl 2-O-methyl (2S,4S)-4-acetyloxypyrrolidine-1,2-dicarboxylate
• CAS: 188109-82-2
• 化学式: C₁₃H₂₁NO₆
• 分子量: 287.313
• InChiKey: OPSHKGZHJLNOAR-UWVGGRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  82.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-Boc-(4S)-acetoxy proline methyl ester 在 sodium periodate 、 ruthenium(III) chloride trihydrate 、 碳酸氢钠 作用下， 以 甲醇 、 水 为溶剂， 反应 24.0h， 生成 dimethyl (2S,4S)-2-hydroxy-4-[(2-methylpropan-2-yl)oxycarbonylamino]pentanedioate
  参考文献：
  名称：

  [EN] MPRO TARGETING ANTIVIRAL COMPOUNDS
  [FR] COMPOSÉS ANTIVIRAUX CIBLANT LES MPRO

  摘要：

  公开了根据式（I）的新型病毒 Mpro 抑制剂、它们的药学上可接受的盐及其药物组合物。还公开了使用此类化合物和组合物抑制 Mpro 和/或治疗各种病毒感染的方法；特别是与冠状病毒有关的病毒感染。本公开的化合物和组合物在治疗广谱冠状病毒方面可能特别有用。

  公开号：

  WO2023180189A1
• 作为产物：
  描述：

  反式-4-羟基-L-脯氨酸甲酯 在 三乙胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 N-Boc-(4S)-acetoxy proline methyl ester
  参考文献：
  名称：

  A convenient and high yield method to prepare 4-hydroxypyroglutamic acids

  摘要：

  RuO2/NaIO4 oxidation of N-Boc-4-silyloxy and 4-acetoxy proline methyl esters under ethyl acetate/water biphase condition gave N-Boc-4-silyloxy and 4-acetoxy pyroglutamic acid derivates in high yields. Desilylation with TBAF afforded both cis- and trans-N-Boc-methyl-4-hydroxy pyroglutamates. (C) 2001 DuPont Pharmaceuticals Company. Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01030-9

文献信息

• Method for Manufacturing Hydroxyl Group Substitution Product
  申请人：Ishii Akihiro

  公开号：US20110251403A1

  公开（公告）日：2011-10-13

  In the present invention, a hydroxyl group substitution product is manufactured by reaction of an alcohol with sulfuryl fluoride (SO 2 F 2 ) in the presence of an organic base and a nucleophile (X − ). The present invention is thus effective as an industrial manufacturing method that uses a relatively cheap reagent suitable for large-scale applications and can be accomplished in a simple process with easy purification operation and less waste generation and is suitably applicable for manufacturing of optically active hydroxyl group substitution products, notably optically active α-hydroxyl group substitution ester and optically active 4-hydroxyl group substitution proline. The manufacturing method of the present invention solves all of the prior art problems and can be applied for industrial uses.

  在本发明中，通过在有机碱和亲核试剂（X^-）存在下，将醇与亚磺酰氟（SO2F2）反应制造羟基取代产物。因此，本发明作为一种工业制造方法是有效的，它使用相对便宜的试剂适用于大规模应用，并且可以在简单的过程中完成，具有易于纯化操作和较少废物生成的特点，适用于制造光学活性的羟基取代产物，特别是光学活性α-羟基取代酯和光学活性4-羟基取代脯氨酸。本发明的制造方法解决了所有先前技术问题，并可应用于工业用途。
• Synthesis of new β- and γ-benzyloxy-S-glutamic acid derivatives and evaluation of their activity as inhibitors of excitatory amino acid transporters
  作者：Lucia Tamborini、Paola Conti、Andrea Pinto、Simona Colleoni、Marco Gobbi、Carlo De Micheli

  DOI：10.1016/j.tet.2009.05.054

  日期：2009.8

  enantiomerically pure diasteroisomers of γ-benzyloxy-S-glutamic acid was performed using trans-4-hydroxy-l-proline as a source of chirality, while the erythro and threo isomers of β-benzyloxy-S-glutamic acid were prepared starting from (R)-Garner's aldehyde. All new derivatives were tested for their inhibitory activity against excitatory amino acid transporters in a rat synaptosomal preparation and their

  γ苄氧基的两个对映体纯非对映异构的有效立体选择性制备小号使用进行谷氨酸反式-4-羟基-升-脯氨酸作为手性源，而赤和苏β苄氧基的异构体小号-从（R）-加纳醛开始制备谷氨酸。测试了所有新衍生物在大鼠突触体制剂中对兴奋性氨基酸转运蛋白的抑制活性，并将其IC 50值与TBOA（一种通常用作谷氨酸转运蛋白的参考阻滞剂的低碳同系物）的IC 50值进行了比较。
• Design and synthesis of simplified taxol analogs based on the T-Taxol bioactive conformation
  作者：Jielu Zhao、Susan Bane、James P. Snyder、Haipeng Hu、Kamalika Mukherjee、Carla Slebodnick、David G.I. Kingston

  DOI：10.1016/j.bmc.2011.10.010

  日期：2011.12

  A series of compounds designed to adopt a conformation similar to the tubulin-binding T-Taxol conformation of the anticancer drug paclitaxel has been synthesized. Both the internally bridged analogs 37-39, 41 and the open- chain analogs 27-29 and 43 were prepared. The bridged analogs 37-39 and 41 were synthesized by Grubbs' metatheses of compounds 30-32 and 33, which, in turn, were prepared by coupling beta-lactams 24-26 with alcohols 22 and 23. Both the bridged and the open- chain analogs showed moderate to good cytotoxicity. (C) 2011 Elsevier Ltd. All rights reserved.