1,2,3,4-tetra-O-acetyl-α-D-galactopyranosiduronic acid | 95722-13-7

• 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-galactopyranosiduronic acid
• 英文别名: 1,2,3,4-tetra-O-acetyl-α-D-galactopyranuronic acid；1,2,3,4-tetra-O-acetyl-α-D-galacturonic acid；(2S,3R,4S,5R,6R)-3,4,5,6-tetraacetoxytetrahydro-2H-pyran-2-carboxylic acid；(2S,3R,4S,5R,6R)-3,4,5,6-tetraacetyloxyoxane-2-carboxylic acid
• CAS: 95722-13-7
• 化学式: C₁₄H₁₈O₁₁
• 分子量: 362.29
• InChiKey: FHWVABAZBHDMEY-LARJDALCSA-N

物化性质

• 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-galactopyranosiduronic acid 在 乙酰溴 、 水 、 氰化汞 、 乙酸酐 、 mercury dibromide 作用下， 以 乙醚 、 氯仿 、 溶剂黄146 为溶剂， 反应 3.0h， 生成 2-丙烯-1-基BETA-D-半乳吡喃糖醛酸甲酯2,3,4-三乙酸酯
  参考文献：
  名称：

  Synthesis of Homogalacturonan Fragments

  摘要：

  Glycosylation of the D-galacturonic acid ester derivatives 15 and 17, which are prepared directly from D-galacturonic acid, with the thioglycosides 28 and 32, derived from the same sugar, provides alpha(1-->4)-linked dimers. The formation of the glycosidic linkage between the galacturonic acid moieties is best achieved by iodonium di-sym-collidine perchlorate promotion. Thus, the 4'-O-p-methoxybenzyl dimer 38 can be obtained in 64% yield. Partial deprotection of the 4'-O-position provided the glycosyl acceptor 36, which was coupled with the donor 32 to yield the alpha(1 "-->4')-linked trimer 39 (48%). Approximately 8% of the beta(1 "-->4')-coupled isomer was observed in the C-13 NMR spectrum of the reaction mixture.

  DOI：

  10.1080/07328300008544125
• 作为产物：
  描述：

  半乳糖醛酸 、 乙酸酐 以 吡啶 为溶剂， 生成 1,2,3,4-tetra-O-acetyl-α-D-galactopyranosiduronic acid
  参考文献：
  名称：

  DEGRADATION REACTION OF α-D-GALACTOPYRANURONIC ACID IN ACETIC ANHYDRIDE-BASE SYSTEM

  摘要：

  α-d-吡喃半乳糖醛酸转化为 1,2,3-三-O-乙酰基-4-脱氧-β-1-苏-4-己烯吡喃糖醛酸 (3) 和 3-乙酰氧基-6-(二乙酰氧基甲基)-2H -吡喃-2-酮分别用乙酸酐-4-(二甲氨基)吡啶或乙酸酐-乙酸-吡啶处理。 3在乙酸酐-三乙胺中进一步降解得到香豆酸。

  DOI：

  10.1246/cl.1985.49

文献信息

• Single Reactant Replacement Approach of Passerini Reaction: One-Pot Synthesis of β-Acyloxyamides and Phthalides
  作者：Yangyong Shen、Bo Huang、Linwei Zeng、Sunliang Cui

  DOI：10.1021/acs.orglett.7b02232

  日期：2017.9.1

  The Passerini reaction is a classical and well-known multicomponent reaction for accessing α-acyloxy amides. A single reactant replacement (SRR) approach of Passerini reaction is described, which involves aldehydes, carboxylic acids, and ynamides to constitute a one-pot synthesis of β-acyloxy amides in a convergent manner. When this method was subject to intramolecular reaction, the process would produce

  Passerini反应是用于获得α-酰氧基酰胺的经典且众所周知的多组分反应。描述了Passerini反应的单反应物置换（SRR）方法，该方法涉及醛，羧酸和乙酰胺，以收敛方式构成β-酰氧基酰胺的一锅法合成。当该方法进行分子内反应时，该过程将产生邻苯二甲酸酯产物。证明了可伸缩性，并进行了交叉反应以阐明合理的机制。
• SnCl₄- and TiCl₄-Catalyzed Anomerization of Acylated <i>O</i>- and <i>S</i>-Glycosides: Analysis of Factors That Lead to Higher α:β Anomer Ratios and Reaction Rates
  作者：Wayne Pilgrim、Paul V. Murphy

  DOI：10.1021/jo101090f

  日期：2010.10.15

  glucuronic acid or galacturonic acid derivatives were ∼10 to 3000 times faster than those of related glucoside and galactopyranoside counterparts and α:β ratios were generally also higher. Stereoelectronic effects contributed from galacto-configured compounds were up to 2-fold faster than those of corresponding glucosides. The introduction of groups, including protecting groups, which are increasingly electron

  讨论了影响SnCl 4和TiCl 4催化的异构化反应速率和立体选择性的因素的定量，以及这如何影响α- O-和α- S-糖脂的合成。SnCl 4催化的18种底物的β- S-和β- O-糖苷的阴离子化反应遵循一级平衡动力学，得到k f + k r值，其中k f是正向反应的速率常数（β→ α）和k r是逆反应的速率常数（α→β）。比较k f + k r值表明，葡萄糖醛酸或半乳糖醛酸衍生物的反应比相关的葡萄糖苷和吡喃半乳糖苷对应物的反应快约10至3000倍，并且α：β比率通常也更高。由半乳糖配置的化合物产生的立体电子效应比相应的糖苷的高达快2倍。越来越多地释放电子的基团（包括保护基）的引入通常导致速率提高。S-糖苷的异构化速度始终快于相应的O-糖苷。与TiCl 4的反应通常比与SnCl 4的反应更快。端基异构体的比例取决于路易斯酸，路易斯酸的当量数，温度和底物。对于TiCl 4促进的反应，观察到O
• Synthesis and Surface‐Active Properties of Uronic Amide Derivatives, Surfactants from Renewable Organic Raw Materials
  作者：Pascal Laurent、Hary Razafindralambo、Bernard Wathelet、Christophe Blecker、Jean‐Paul Wathelet、Michel Paquot

  DOI：10.1007/s11743-010-1205-8

  日期：2011.1

  chemical syntheses were developed to produce a new set of surfactants from uronic acids derived from widely available raw materials. Three different strategies were used to synthesize uronic amide derivatives, the structures of which were totally characterized by spectrometric methods (IR, MS, 1H‐RMN and 13C‐RMN). The best one, using an acid chloride as the synthetic intermediate, furnished the expected amides

  开发了短的化学合成方法，以从可广泛获得的原料中获得的糖醛酸生产一套新的表面活性剂。三种不同的策略被用于合成糖醛酰胺衍生物，其结构通过光谱法（IR，MS，1 H-RMN和13 C-RMN）完全表征。最好的化合物是使用酰氯作为合成中间体，以46-58％的全球收率提供了预期的酰胺，为各种异构体的混合物。表面活性性质（CMC，γ CMC，Γ最大，甲分钟）的同系物的糖醛酸Ñ还评估了C8至C18的烷基酰胺。通常，与最著名的非离子表面活性剂辛基苯酚9-10环氧乙烷缩合物相比，这些糖基表面活性剂表现出良好的表面活性，并且是有价值的非离子表面活性剂。烷基链长度的增加会影响葡萄糖醛糖醛和半乳糖醛酸N-烷基酰胺衍生物的CMC值。半乳糖醛Ñ -alkylamides降低γ CMC在比其对应的醛值慢Ñ -alkylamides。
• Synthesis of α-galactosyl ceramide analogues with an α-triazole at the anomeric carbon
  作者：Anthony W. McDonagh、Paul V. Murphy

  DOI：10.1016/j.tet.2014.03.029

  日期：2014.5

  The synthesis of 1,2,3-triazole containing analogues of α-GalCer and galacturonic acid containing Sphingomonous cell wall antigens is described. Anomerisation was used to provide the required α-glycosyl azide precursor. Copper azide–alkyne cycloaddition (CuAAC) generated the α-triazole linkage.

  描述了含有1,2,3-三唑的α-GalCer类似物和含有半乳糖醛酸的狮壁细胞壁抗原的合成。使用异构化来提供所需的α-糖基叠氮化物前体。叠氮化铜-炔烃环加成反应（CuAAC）生成α-三唑键。
• Synthesis of methyl (d-glycopyranosyl azide) uronates
  作者：Zoltán Györgydeák、Joachim Thiem

  DOI：10.1016/0008-6215(94)00313-5

  日期：1995.3

  Abstract Sodium hypochlorite oxidation catalysed by 2,2,6,6,-tetramethylpiperidine 1-oxide (TEMPO) is shown to be a mild and efficient approach to the title uronates. In the gluco, galacto, allo , and 2-acetamido-2-deoxy- gluco series, the corresponding β- or α- and β-glycosyl azides could be smoothly oxidised and alternative preparations are compared to this access.

  摘要显示了由2,2,6,6，-四甲基哌啶1-氧化物（TEMPO）催化的次氯酸钠氧化是一种温和而有效的标题尿酸盐的方法。在葡萄糖，半乳糖，同素和2-乙酰氨基-2-脱氧-葡萄糖系列中，相应的β-或α-和β-糖基叠氮化物可以被平滑地氧化，并将替代制剂与这种方法进行比较。