1,2,3,4-tetra-O-acetyl-α-D-glucopyranuronic acid | 83023-73-8

• 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: 1,2,3,4-tetra-O-acetyl-α-D-glucopyranuronic acid
• 英文别名: (2S,3S,4S,5R,6R)-3,4,5,6-tetraacetoxytetrahydro-2H-pyran-2-carboxylic acid；(2S,3S,4S,5R,6R)-3,4,5,6-tetraacetyloxyoxane-2-carboxylic acid
• CAS: 83023-73-8
• 化学式: C₁₄H₁₈O₁₁
• 分子量: 362.29
• InChiKey: FHWVABAZBHDMEY-GCQYFTOKSA-N

物化性质

• 熔点：
  118-119 °C(Solv: ethanol (64-17-5))
• 沸点：
  458.3±45.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  152
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  1,2,3,4-tetra-O-acetyl-α-D-glucopyranuronic acid 在 N-甲基吗啉 、 间氯过氧苯甲酸 、 氯甲酸异丁酯 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 6,7-dideoxy-1,2:3,4-tetra-O-acetyl-7-phenylsulphonyl-7-α-L-ido-6-ene-heptopyranose
  参考文献：
  名称：

  Stereocontrolled radical reactions in carbohydrate and nucleoside chemistry.

  摘要：

  The radicals, generated by photolysis of 2,3-dimethyl ketals of N-hydroxy-2- thiopyridone uronic esters, reacted stereoselectively with electron deficient olefins leading to highly functionalised chain-elongated pentafuranosides, hexapyranosides and pentafuranosyl-nucleosides through the 4,5 and 4' radicals, respectively.

  DOI：

  10.1016/s0957-4166(00)86288-6
• 作为产物：
  描述：

  1,2,3,4-tetra-O-acetyl-α-D-glucuronamide 在 potassium acetate 、 二氧化氮 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以75%的产率得到1,2,3,4-tetra-O-acetyl-α-D-glucopyranuronic acid
  参考文献：
  名称：

  Stereocontrolled radical reactions in carbohydrate and nucleoside chemistry.

  摘要：

  The radicals, generated by photolysis of 2,3-dimethyl ketals of N-hydroxy-2- thiopyridone uronic esters, reacted stereoselectively with electron deficient olefins leading to highly functionalised chain-elongated pentafuranosides, hexapyranosides and pentafuranosyl-nucleosides through the 4,5 and 4' radicals, respectively.

  DOI：

  10.1016/s0957-4166(00)86288-6

文献信息

• Synthesis, characterization, and conformation in solution of a novel d-glucurono-6,1-lactam derivative
  作者：Yasuko Takeda、Toshio Akimoto、Yoshimasa Kyogoku

  DOI：10.1016/s0008-6215(00)81072-1

  日期：1982.8

  6-lactam ( 2 ), a novel d -glucorono-6,1-lactam derivative. Its conformation in solution, examined by 1 H- and 13 C-n.m.r. and compared with the crystal structure, corresponds to a fairly rigid ring system, the pyranose ring adopting a near B O,3 ( d ) boat form in solution and a distorted 1 C 4 ( d ) chair conformation in the crystalline state. The closely related 2,3,4-tri- O -acetyl-β- d -glucopyranurono-6

  摘要在吡啶存在下，于室温下用乙酸酐将2'-（β-d-葡萄糖基吡喃葡萄糖基尿酸酯钠）异烟酰肼在室温下延长处理约110小时，得到2,3,4-三-O-乙酰基-N-（二乙酰氨基）- β-d-葡萄糖吡喃并-1,6-内酰胺（2），一种新的d-葡萄糖基-6,1-内酰胺衍生物。由1 H-和13 Cn.mr检查并在溶液中的构象，并与晶体结构进行比较，它对应于一个相当刚性的环系统，吡喃糖环在溶液中采用接近BO，3（d）的船形，并扭曲了1 C 4（d）椅构型呈结晶态。密切相关的2,3,4-tri-O-乙酰基-β-d-吡喃葡萄糖醛-6,1-内酯（4）和2,3,4-tri-O-乙酰基-1,6-脱水-β- d-葡萄糖（3）呈扭曲的1 C 4（d）构象，呈溶液形式和晶体形式。根据4的晶体结构数据，
• Glycosidation–Anomerisation Reactions of 6,1-Anhydroglucopyranuronic Acid and Anomerisation of β-D-Glucopyranosiduronic Acids Promoted by SnCl4
  作者：Colin O'Brien、Monika Poláková、Nigel Pitt、Manuela Tosin、Paul V. Murphy

  DOI：10.1002/chem.200601111

  日期：2007.1.12

  onic acids was found to be faster, in some cases, than anomerisation of related beta-D-glucopyranosiduronic acid esters and beta-D-glucopyranoside derivatives and the rates are dependent on the structure of the aglycon. Moreover, the rates of anomerisation of beta-D-glucopyranuronic acid derivatives can be qualitatively correlated with rates of hydrolysis of beta-D-glucopyranosiduronic acids. Mechanistic

  氯化锡（IV）催化的甲硅烷基化亲核试剂与6,1-脱水葡萄糖基吡喃糖醛酸（葡萄糖醛酸6,1-内酯）的反应提供了1,2-反式或1,2-顺式（脱氧）糖苷，具体取决于供体结构。对于供体与2-酰基和2-脱氧供体的反应，获得了α-糖苷，而2-脱氧-2-碘的供体给出了β-糖苷。实验证据表明，当1,2-顺式糖苷形成时，由SnCl（4）催化的最初形成的1,2-反式糖苷的异构化是可能的。在某些情况下，发现β-D-吡喃葡萄糖苷神经酸酯的异构化比相关的β-D-吡喃葡萄糖苷神经酸酯和β-D-吡喃葡萄糖苷衍生物的异构化更快，并且速率取决于糖苷配基的结构。而且，β-D-吡喃葡萄糖醛酸衍生物的异构化速率可以与β-D-吡喃葡萄糖醛糖醛酸的水解速率定性相关。考虑了反应的机械可能性。
• Synthesis of Thioesters from Carboxylic Acids via Acyloxyphosphonium Intermediates with Benzyltriethylammonium Tetrathiomolybdate as the Sulfur Transfer Reagent
  作者：Purushothaman Gopinath、Ravindran Sasitha Vidyarini、Srinivasan Chandrasekaran

  DOI：10.1021/jo9009694

  日期：2009.8.21

  An efficient protocol is reported for the synthesis of thioesters from carboxylic acids with use of acyloxy phosphonium salts as intermediates and benzyltriethylammonium tetrathiomolybdate as the sulfur transfer reagent

  据报道，使用酰氧基phospho盐作为中间体，用苄基三乙基铵四硫代钼酸铵作为硫磺转移试剂，可以有效地从羧酸合成硫酯。
• Ester linkages between lignin and glucuronic acid in lignin-carbohydrate complexes from Fagus crenata
  作者：Takeshi Imamura、Takashi Watanabe、Masaaki Kuwahara、Tetsuo Koshijima

  DOI：10.1016/s0031-9422(00)89551-5

  日期：1994.11

  trifluoroacetic acid (TFA) was applied to the binding site analysis of ester linkages between lignin and glucuronoxylan in Fagus crenata wood. Based on the conjugate acid DDQ-oxidation of a watersoluble lignin-carbohydrate complex (LCC-WE) from the beech wood, the frequency of the ester bonds between the lignin and glucuronic acid residue of glucuronoxylan was determined to be 1.6 per molecule of LCC-WE

  摘要 苄基酯与 2,3-二氯-5,6-二氰基-1,4-苯醌 (DDQ) 和三氟乙酸 (TFA) 的共轭酸氧化应用于 FAgus 木质素和葡糖醛酸木聚糖之间酯键的结合位点分析克雷纳塔木。基于来自山毛榉木材的水溶性木质素 - 碳水化合物复合物 (LCC-WE) 的共轭酸 DDQ 氧化，木质素和葡糖醛酸木聚糖的葡糖醛酸残基之间的酯键频率被确定为每分子 LCC-1.6我们。
• High-yielding syntheses of hydrophilic conjugatable chlorins and bacteriochlorins
  作者：Jason R. McCarthy、Jayeeta Bhaumik、Nabyl Merbouh、Ralph Weissleder

  DOI：10.1039/b908713c

  日期：——

  Next-generation photodynamic therapy agents based upon the conjugation of multiple photosensitizers to a targeting backbone will allow for more efficacious light-based therapies. To this end, we have developed glucose-modified chlorins and bacteriochlorins featuring a reactive carboxylic acid linker for conjugation to targeting moieties. The photosensitizers were synthesized in relatively high yields from meso-tetra(p-aminophenyl)porphyrin, and resulted in neutral, hydrophilic chromophores with superb absorption profiles in the far-red and near-infrared portions of the electromagnetic spectrum. In addition, conjugation of these photosensitizers to a model nanoscaffold (crosslinked dextran-coated nanoparticles) demonstrated that the inclusion of hydrophilic sugar moieties increased the number of dyes that can be loaded while maintaining suspension stability. The described compounds are expected to be particularly useful in the synthesis of a number of targeted nanotherapeutic systems.

  基于将多种光敏剂与靶向骨架共轭的下一代光动力疗法制剂将使基于光的疗法更加有效。为此，我们开发了葡萄糖修饰的氯素和细菌氯素，它们具有活性羧酸连接体，可与靶向分子连接。这些光敏剂是由中-四（对氨基苯基）卟啉以相对较高的产率合成的，并产生了中性亲水性发色团，在电磁波谱的远红外和近红外部分具有极好的吸收曲线。此外，将这些光敏剂与模型纳米支架（交联葡聚糖涂层纳米粒子）共轭的结果表明，亲水性糖分子的加入增加了可负载的染料数量，同时保持了悬浮稳定性。所描述的化合物有望在合成一些靶向纳米治疗系统中发挥特别的作用。