2-(((3aR,5R,6S,6aR)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-yl)oxy)acetic acid | 64697-82-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(((3aR,5R,6S,6aR)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-yl)oxy)acetic acid
• 英文别名: 2-[[(3aR,5R,6S,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl]oxy]acetic acid
• CAS: 64697-82-1
• 化学式: C₁₄H₂₂O₈
• 分子量: 318.324
• InChiKey: PQJQDUMTNKVEQJ-DVYMNCLGSA-N

物化性质

• 沸点：
  447.6±45.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  92.7
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-(((3aR,5R,6S,6aR)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-yl)oxy)acetic acid 在 碳酸氢钠 、 N,N'-二环己基碳二亚胺 作用下， 以 1,2-二氯乙烷 、 乙腈 为溶剂， 生成 (S)-2-{2-[(3aR,5R,6S,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy]-acetylamino}-propionic acid
  参考文献：
  名称：

  Synthesis of conjugates of glyco amino acids and glycopeptides with carboxylic acid hydrazides

  摘要：

  DOI：

  10.1007/bf02254806
• 作为产物：
  描述：

  t-butyl3-O-carboxymethyl-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 在 水 、 sodium hydroxide 作用下， 反应 2.0h， 生成 2-(((3aR,5R,6S,6aR)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-yl)oxy)acetic acid
  参考文献：
  名称：

  [EN] INHIBITORS OF MALARIAL AND PLASMODIUM FALCIPARUM HEXOSE TRANSPORTER AND USES THEREOF
  [FR] INHIBITEURS DU TRANSPORTEUR D'HEXOSE DE LA MALARIA ET DE PLASMODIUM FALCIPARUM ET LEURS UTILISATIONS

  摘要：

  提供了能够结合到疟原虫己糖转运蛋白（PfHT）或其类似物的结合口袋的分子，以及包含这些分子的复合物。此外，还提供了PfHT的抑制剂，包含这些抑制剂的药物组合物，以及在治疗与疟原虫或PfHT相关的疾病或杀死或抑制疟原虫生长中使用这些抑制剂或药物组合物的方法。提供了这些结合口袋的结构坐标集合，并提供了使用这些结构坐标集合来筛选和设计能够结合到PfHT或其类似物的化合物的方法。

  公开号：

  WO2021155748A1

文献信息

• Versatile Approaches to Sugar Amino Acid Building Blocks as Precursors of Glycopeptides
  作者：Christelle Jablonski-Lorin、Matthias Nold、Arthur Bodenmüller、Ernst Hungerbühler

  DOI：10.2533/chimia.2006.286

  日期：——

  The synthesis of monosaccharide units functionalised with different amino acids is described herein. Sugar amino acid templates linked at position 6 of the sugar were prepared by various nucleophilic substitutions introducing a spacer of variable length or by traceless Staudinger ligation. Sugar amino acid templates attached at the anomeric position and representing a class of precursors of glycopeptides were synthesized in three steps via addition of a solution of trimethylsilylnitrate-trimethylsilylazide on a glycal, followed by subsequent reduction of the sugar azide and coupling with diverse amino acids.

  本文描述了具有不同氨基酸功能化的单糖单元的合成。在糖的第6位连接的糖氨基酸模板通过各种亲核取代制备，引入可变长度的间隔或无痕Staudinger缩合。连接在缩醛位置并代表一类糖肽前体的糖氨基酸模板通过在糖醛上加入三甲基硅硝酸酯-三甲基硅叠氮化物溶液，随后还原糖叠氮化合物并与多种氨基酸偶联，经过三步合成。
• Electrochemical Site‐Selective Alkylation of Tropones via Formal C(<i>sp</i>³)−C(<i>sp</i>²) Coupling Reaction
  作者：Andrea Brunetti、Mauro Garbini、Nico Gino Kub、Magda Monari、Riccardo Pedrazzani、Chiara Zanardi、Giulio Bertuzzi、Marco Bandini

  DOI：10.1002/adsc.202400050

  日期：——

  The first site‐selective electrochemical alkylation of tropones is realized by reacting 2‐acetoxytropones and redox‐active‐esters. The electroreductive protocol enables the preparation of a wide range (27 examples) of mono‐ and disubstituted tropones in high yields (up to 71%) and very mild conditions. Dedicated voltammetric measurements served for the identification of 2‐acetoxytropones as a class

  托酮的第一个位点选择性电化学烷基化是通过 2-乙酰氧基托酮和氧化还原活性酯的反应实现的。电还原方案能够以高收率（高达 71%）和非常温和的条件制备各种（27 个示例）单取代和二取代托酮。专用伏安测量用于鉴定 2-乙酰氧基托酮作为一类有价值的亲核自由基捕获剂，并揭示整个机理。对传统官能团的广泛耐受性（27 个示例）以及对生物活性化合物后期功能化的应用，强调了本方法的合成影响
• 4-Acetamidophenyl esters and 4-acetamidoanilides of L-arginine,p-guanidino-L-phenylalanine, L-lysine, N2-[D-fructos-3-O-yl and D-glucos-3-O-yl]acetyl-L-lysine as potential acrosin inhibitors
  作者：R.Alan Chrusciel、Ludwig Bauer、JoAnne M. Kaminski、Lourens J.D. Zaneveld

  DOI：10.1016/s0040-4020(01)80998-4

  日期：1991.10

  Syntheses of 4-acetamidophenyl esters and 4-acetamidoanilides of L-lysine,p-guanidino-L-phenylalanine, L-leucyl-L-lysine, L-leucyl-L-leucyl-L-lysine, N2-[(1,2-O-isopropylidene-alpha-D-glucofuranos-3-O-yl)acetyl]-L-lysine, N2-[(1,2-O-isopropylidene-beta-D-fructopyranos-3-O-yl)acetyl]-L-lysine are reported. 4-Acetamidophenyl L-argininate was too unstable to be isolated but L-arginin-4-acetamidoanilide was prepared. These amino acid and peptide derivatives proved to be enantiomerically pure and were characterized by their H-1 and C-13 chemical shifts which were established by means of multipulse 1D and 2D NMR techniques. Preliminary evaluation showed these compounds to be relatively weak inhibitors of human acrosin and bovine trypsin.
• [EN] INHIBITORS OF MALARIAL AND PLASMODIUM FALCIPARUM HEXOSE TRANSPORTER AND USES THEREOF<br/>[FR] INHIBITEURS DU TRANSPORTEUR D'HEXOSE DE LA MALARIA ET DE PLASMODIUM FALCIPARUM ET LEURS UTILISATIONS
  申请人：UNIV TSINGHUA

  公开号：WO2021155748A1

  公开（公告）日：2021-08-12

  Provided are molecules capable of binding to binding pockets of Plasmodium falciparum hexose transporter (PfHT) or analogs thereof and complexes comprising the same. Also provided herein are inhibitors of PfHT, pharmaceutical compositions comprising the inhibitors, and methods of using the inhibitors or the pharmaceutical compositions in the treatment of diseases associated with Plasmodium or PfHT or the killing or inhibiting the growth of Plasmodium. Provided are a set of structure coordinates of such binding pockets and method of using the set of structure coordinates to screen for and design compounds that are capable of binding to PfHT or analogs thereof.

  提供了能够结合到疟原虫己糖转运蛋白（PfHT）或其类似物的结合口袋的分子，以及包含这些分子的复合物。此外，还提供了PfHT的抑制剂，包含这些抑制剂的药物组合物，以及在治疗与疟原虫或PfHT相关的疾病或杀死或抑制疟原虫生长中使用这些抑制剂或药物组合物的方法。提供了这些结合口袋的结构坐标集合，并提供了使用这些结构坐标集合来筛选和设计能够结合到PfHT或其类似物的化合物的方法。
• Synthesis of conjugates of glyco amino acids and glycopeptides with carboxylic acid hydrazides
  作者：A. E. Zemlyakov、V. O. Kur'yanov、V. N. Tsikalova、V. Ya. Chirva

  DOI：10.1007/bf02254806

  日期：1997.9