methyl 2,3,4,6-tetra-O-methylgalactopyranoside | 14187-59-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,4,6-tetra-O-methylgalactopyranoside
• 英文别名: (3R,4S,5S,6R)-2,3,4,5-tetramethoxy-6-(methoxymethyl)oxane
• CAS: 14187-59-8
• 化学式: C₁₁H₂₂O₆
• 分子量: 250.292
• InChiKey: ZYGZAHUNAGVTEC-FNIJGJLWSA-N

物化性质

• 沸点：
  142-145 °C(Press: 12 Torr)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4,6-tetra-O-methylgalactopyranoside 、 盐酸 、 水 生成 (3R,4S,5S,6R)-3,4,5-Trimethoxy-6-methoxymethyl-tetrahydro-pyran-2-ol
  参考文献：
  名称：

  NOE, CHRISTIAN R.;KNOLLMULLER, MAX;ETTMAYER, PETER, LIEBIGS ANN. CHEM.,(1991) N, C. 417-424

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl ether of thalicoside 在 盐酸 作用下， 生成 methyl-2,3,4,6-tetra-O-methyl-D-glucopyranoside 、 methyl 2,3,4,6-tetra-O-methylgalactopyranoside
  参考文献：
  名称：

  Triterpene saponins fromThalictrum minus. IV. The structure of thalicoside A

  摘要：

  DOI：

  10.1007/bf00579482

文献信息

• Saponin and sapogenol. XXXVIII. Structure of soyasaponin A2, a bisdesmoside of soyasapogenol A, from soybean, the seeds of Glycine max Merrill.
  作者：ISAO KITAGAWA、MASAYUKI SAITO、TOSHIO TANIYAMA、MASAYUKI YOSHIKAWA

  DOI：10.1248/cpb.33.598

  日期：——

  Two new bisdesmosides of soyasapogenol A (1), named soyasaponin A1 and soyasaponin A2 (7), were isolated from soybean, the seeds of Glycine max MERRILL, together with the known soyasaponins I (4), II (5), and III (6). By employing a photochemical degradation method, which is a selective cleavage method for the glucuronide linkage in oligoglycosides, and on the bases of spectral analyses and chemical reactions, the structure of soyasaponin A2 was elucidated as 3-O-[β-D-galactopyranosyl (1→2)-β-D-glucuronopyranosyl]-22-O-[β-D-glucopyranosyl (1→3)-α-L-arabinopyranosyl] soyasapogenol A (7).

  从大豆（Glycine max MERRILL的种子）中分离出两种新的大豆皂醇A（1）的双糖苷，命名为大豆皂苷A1和大豆皂苷A2（7），以及已知的大豆皂苷I（4）、II（5）和III（6）。通过采用光化学降解方法，这是一种针对寡糖苷中葡萄糖醛酸键的选择性断裂方法，并基于光谱分析和化学反应，确定了大豆皂苷A2的结构为3-O-[β-D-半乳糖吡喃糖基（1→2）-β-D-葡萄糖醛酸吡喃糖基]-22-O-[β-D-葡萄糖吡喃糖基（1→3）-α-L-阿拉伯糖吡喃糖基]大豆皂醇A（7）。
• Saponin and sapogenol. XXXIX. Structure of soyasaponin A1, a bisdesmoside of soyasapogenol A, from soybean, the seeds of Glycine max Merrill.
  作者：ISAO KITAGAWA、MASAYUKI SAITO、TOSHIO TANIYAMA、MASAYUKI YOSHIKAWA

  DOI：10.1248/cpb.33.1069

  日期：——

  Five bioactive triterpene-oligoglycosides, named soyasaponins I, II, III, A1 (3), and A2 (2), were isolated from soybean, the seeds of Glycine max MERRILL (Leguminosae). By employing a photochemical degradation method and a lead tetraacetate degradation method, which are two of four selective cleavage methods available for the glucuronide linkage in oligoglycosides, the structure of soyasaponin A1 was elucidated to be 3-O [β-D-glucopyranosyl (1→2)-β-D-galactopyranosyl (1→2)-β-D-glucuronopyranosyl-22-O-[β-D-glucopyranosyl (1→3)-α-L-arabinopyranosyl]-soyasapogenol A (3).

  从豆科植物大豆（Glycine max Merrill）的种子中分离出五种具有生物活性的三萜类低聚糖苷，分别命名为大豆皂苷I、II、III、A1（3）和A2（2）。通过采用两种选择性裂解方法，即光化学降解法和四乙酸铅降解法（这是四种可用于低聚糖苷中葡萄糖醛酸连接的选择性裂解方法中的两种），阐明了大豆皂苷A1的结构为：3-O[β-D-葡萄吡喃糖基（1→2）-β-D-半乳吡喃糖基（1→2）-β-D-葡萄糖醛吡喃糖基]-22-O[β-D-葡萄吡喃糖基（1→3）-α-L-阿拉伯吡喃糖基]-大豆皂苷元A（3）。
• Triterpene and steroidal glycosides from the genus Melilotus and their genins.
  作者：G. V. Khodakov

  DOI：10.1007/s10600-010-9678-2

  日期：2010.9

  melilotosides A1, B1, and C1, and non-glycosylated soyasapogenol B were isolated from Melilotus officinalis (L.) Pall. (Fabaceae) roots. The structures of the glycosides were proved using chemical transformations and spectral data. Melilotoside A1 is soyasapogenol B 3-O-β-Dxylopyranoside; melilotoside B1, soyasapogenol B 3-O-[β-D-galactopyranosyl-(1-2)-f-D-xylopyranoside]; melilotoside C1, soyasapogenol B 3-O

  从 Melilotus officinalis (L.) Pall 中分离出三种新的三萜齐墩果苷、苜蓿苷 A1、B1 和 C1，以及非糖基化大豆皂醇 B。（豆科）根。使用化学转化和光谱数据证明了糖苷的结构。苜蓿苷 A1 是大豆皂醇 B 3-O-β-吡喃木糖苷；苜蓿苷 B1，大豆皂苷 B 3-O-[β-D-吡喃半乳糖基-(1-2)-fD-吡喃木糖苷]；melilotoside C1, soyasapogenol B 3-O-[α-L-rhamnopyranosyl-(1-2)-β-D-galactopyranosyl(1-2)-β-Dxylopyranoside]。
• A gas-to-solid phase methanolysis method for the analysis of small amounts of oligosaccharides
  作者：Daniel Derbie Asres、Hélène Perreault

  DOI：10.1139/v96-168

  日期：1996.8.1

  A gas-to-solid phase methanolysis method for the analysis of oligosaccharides is presented. The advantages of using this new gas-to-solid phase method, as opposed to conventional bulk phase techniques, are described, along with comparisons of results obtained from both techniques. The reliable bulk phase methanolysis methods are used as benchmarks for assessing the extent of completion of the gas-to-solid reactions. Gas chromatographic – mass spectrometric (GC–MS) data show that, in general, higher temperatures and longer reaction times are required for completion of the gas-to-solid methanolysis process than for completion of the bulk phase reaction. On the other hand, the gas-to-solid procedure requires only minimal amounts of substrate that would be difficult to characterize using bulk phase methanolysis due to losses during clean-up procedures. Gas-to-solid methanolysis reactions of permethylated di- and trisaccharides were investigated (GC–FID and GC–MS), following initial experiments performed in order to characterize the GC retention times and mass spectra of permethylated standard monosaccharides. Conversion of neutral disaccharides, as well as neutral and acidic trisaccharides, to their respective monosaccharides was successful using the gas-to-solid method. The GC–FID and GC–MS traces show that the gas-to-solid method gives a cleaner reaction than the bulk phase method. Key words: oligosaccharides, methanolysis, permethylation, gas chromatography – mass spectrometry, mass spectrometry.

  本文介绍了一种气-固相甲醇解法用于分析低聚糖。与传统的大量相技术相比，使用这种新的气-固相方法的优点被描述，并对两种技术得到的结果进行了比较。可靠的大量相甲醇解法被用作评估气-固反应完成程度的基准。气相色谱-质谱（GC-MS）数据表明，通常需要更高的温度和更长的反应时间才能完成气-固相甲醇解过程，而不是完成大量相反应。另一方面，气-固过程仅需要少量的底物，这些底物在清洁过程中很难用大量相甲醇解法表征。对甲基化的二糖和三糖进行了气-固相甲醇解反应的研究（GC-FID和GC-MS），并进行了初步实验以表征甲基化标准单糖的GC保留时间和质谱图。使用气-固法成功地将中性二糖以及中性和酸性三糖转化为它们各自的单糖。GC-FID和GC-MS图表明，与大量相法相比，气-固法给出了更干净的反应。关键词：低聚糖，甲醇解，甲基化，气相色谱-质谱，质谱。
• Soybean saponins, and a method of isolating the same
  申请人：Osaka Chemical Laboratory Co., Ltd.

  公开号：US04524067A1

  公开（公告）日：1985-06-18

  This invention is directed to new saponins isolated from soybean seeds, a method for isolating the same and uses of the saponin component of soybeans as an antioxidant for foodstuffs or cosmetics and as an agent for affecting the metabolism in human beings.

  本发明涉及从大豆种子中分离出的新皂苷，一种分离它们的方法以及大豆皂苷成分作为食品或化妆品抗氧化剂和影响人体新陈代谢的药剂的用途。