1,2,3,4-tetra-O-acetyl-α-D-galactopyranosiduronic acid, methyl ester | 30628-07-0

• 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, methyl ester
• 英文别名: methyl 1,2,3,4-tetra-O-acetyl-α-D-galactopyranosiduronate；Methyl(1,2,3,4-tetra-O-acetyl-α-D-galactopyranose)uronat；Methyl 1,2,3,4-tetra-O-acetyl-α-D-galactopyranuronate；tetra-O-acetyl-α-D-galactopyranuronic acid methyl ester；Tetra-O-acetyl-α-D-galactopyranuronsaeure-methylester；Methyl(1,2,3,4-tetra-O-acetyl-α-D-galactopyranosid)uronat；1,2,3,4-Tetra-O-acetyl-A-D-galacturonic acid methyl ester；methyl (2S,3R,4S,5R,6R)-3,4,5,6-tetraacetyloxyoxane-2-carboxylate
• CAS: 30628-07-0
• 化学式: C₁₅H₂₀O₁₁
• 分子量: 376.317
• InChiKey: DPOQCELSZBSZGX-KDBYPZKRSA-N

物化性质

• 熔点：
  142-143 °C
• 沸点：
  412.3±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)：
  -0.3
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  141
• 氢给体数：
  0
• 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, methyl ester 在 乙酰溴 、 水 、 氰化汞 、 乙酸酐 、 mercury dibromide 作用下， 以 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：

  D-galacturonic acid monohydrate 在 高氯酸 、 碳酸氢钠 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成 1,2,3,4-tetra-O-acetyl-α-D-galactopyranosiduronic acid, methyl ester
  参考文献：
  名称：

  在异头碳原子上与α-三唑合成α-半乳糖基神经酰胺类似物

  摘要：

  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。

  DOI：

  10.1016/j.tet.2014.03.029

文献信息

• 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 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。
• Site-Selective Photobromination of O-Acetylated Carbohydrates in Benzotrifluoride
  作者：Guoqing Zhang、Nicholas W. See、Norbert Wimmer、Michael J. Godinez、Scott A. Cameron、Richard H. Furneaux、Vito Ferro

  DOI：10.1021/acs.orglett.4c01898

  日期：2024.7.19

  Ferrier photobromination enables direct synthetic access to valuable 5-C-bromosugars but has limitations that restrict its broader use. The reaction is typically conducted in CCl4 heated at reflux with irradiation by broad spectrum, energy-inefficient heat lamps. Herein, we demonstrate that the reaction proceeds rapidly and efficiently with PhCF3 as a safe and environmentally benign alternative to

  Ferrier 光溴化可以直接合成有价值的 5- C-溴糖，但其局限性限制了其更广泛的应用。该反应通常在用广谱、低能效热灯照射回流加热的CCl 4中进行。在此，我们证明，在配有紫色发光二极管 (LED) 的紧凑型光反应器内，使用 PhCF 3作为 CCl 4的安全且环保的替代品，反应在温和温度 (≤ 40 °C) 下快速​​有效地进行。
• Regioselective green anomeric deacetylation catalyzed by lanthanide triflates
  作者：Anh Tuan Tran、Sophie Deydier、David Bonnaffé、Christine Le Narvor

  DOI：10.1016/j.tetlet.2008.01.106

  日期：2008.3

  Lanthanide triflates, especially Nd(OTf)(3), efficiently catalyze the regioselective transesterification of anomeric acetates. This method offers an efficient solution for the otherwise difficult removal of methyl uronates anomeric acetates as well as a green alternative to published protocols since the lanthanide catalysts are non-toxic and may be easily recycled and reused. (c) 2008 Elsevier Ltd. All rights reserved.
• Vogel, Chr.; Boye, H.; Kristen, H., Journal fur praktische Chemie (Leipzig 1954), 1990, vol. 332, # 1, p. 28 - 36
  作者：Vogel, Chr.、Boye, H.、Kristen, H.

  DOI：——

  日期：——