4-O-吡喃半乳糖基-3,6-去氢半乳糖二甲基缩醛 | 20379-41-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 4-O-吡喃半乳糖基-3,6-去氢半乳糖二甲基缩醛
• 英文名称: 4-O-β-D-galactopyranosyl-3,6-anhydro-L-galactose dimethylacetal
• 英文别名: Agarobiose-dimethylacetal；4-O-Galactopyranosyl-3,6-anhydrogalactose dimethylacetal；(2S,3R,4S,5R,6R)-2-[(2S,3R,4S)-4-hydroxy-2-[(1S)-1-hydroxy-2,2-dimethoxyethyl]oxolan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 20379-41-3
• 化学式: C₁₄H₂₆O₁₁
• 分子量: 370.354
• InChiKey: ZIWAHEUMIYTNAM-XQEHQGFQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.7
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  168
• 氢给体数：
  6
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 4-O-吡喃半乳糖基-3,6-去氢半乳糖二甲基缩醛 在 吡啶 作用下， 生成 Hexa-O-acetyl-agarobiose-dimethylacetyl
  参考文献：
  名称：

  Isolation of Agarobiose Derivative from the Mucilage of Gloiopeltis Furcata

  摘要：

  1. Gloiopeltis furcata 的黏液经过部分甲醇解作用，最终分离出甲基 d-半乳糖苷、3,6-脱水-l-半乳糖二甲基缩醛、甲基 d-木糖苷和琼脂二糖二甲基缩醛。2. 由于琼脂二糖衍生物获得了较好的产率，因此可以断定，该二糖代表了黏液分子的主要重复单元，前提是忽略黏液中存在的硫酸盐残基。3. 目前为止，木糖被首次确认与 Gloiopeltis 的黏液相关。但由于产率极低，该糖可能源自污染的木聚糖。

  DOI：

  10.1246/bcsj.31.428
• 作为产物：
  描述：

  甲醇 、 alkaline earth salt of/the/ methylsulfuric acid 在 mercury dichloride 、 mercury(II) oxide 作用下， 生成 4-O-吡喃半乳糖基-3,6-去氢半乳糖二甲基缩醛
  参考文献：
  名称：

  Studies on the Chemical Constitution of Agar-agar. XVII Isolation of Crystalline Agarobiose Dimethylacetal by Partial Methanolysis of Agar-agar

  摘要：

  DOI：

  10.1246/bcsj.27.109

文献信息

• Studies on the Chemical Constitution of Agar-agar. XIX. Pyruvic Acid as a Constituent of Agar-agar (Part 3). Structure of the Pyruvic Acid-linking Disaccharide Derivative Isolated from the Methanolysis Products of Agar
  作者：Susumu Hirase

  DOI：10.1246/bcsj.30.75

  日期：1957.1

  1. The structure of the acidic compound, isolated from the partial metha-nolysis products of agar in the previous work, has been investigated.2. Methylation data have indicated that the structure of the compound is 4-O-4′, 6′-O-1″-carboxyethylidene-β-d-galactopyranosyl-3,6-anhydro-l-galactose dimethyl-acetal, the β-linkage being suggested on the basis of the optical rotatory behavior.3. The structure assigned is also supported by the result of partial hydrolysis and periodate oxidation of the compound.4. No information has been obtained as to the configuration of the carbon atom C1 of the ethylidene group in the molecule.

  1. 在之前的研究中，从琼脂的部分甲醇解离产物中分离得到的酸性化合物的结构已经被研究。 2. 甲基化数据表明该化合物的结构为4-O-4′, 6′-O-1″-羧乙烯基-β-d-半乳糖吡喃糖-3,6-脱水-l-半乳糖二甲基缩醛，β-连接基因据光学旋转行为推测。 3. 所赋予的结构也得到了该化合物的部分水解和期亚硫酸盐氧化的结果支持。 4. 目前尚未获得关于分子中乙烯基团C1碳原子构型的信息。
• Regioselectivity in Sulfation of Galactosides by Sulfuric Acid and Dicyclobexylcarbodi-imide
  作者：Ryo Takano、Takashi Ueda、Yasuhide Uejima、Kaeko Kamel-Hayashi、Saburo Hara、Susumu Hirase

  DOI：10.1271/bbb.56.1413

  日期：1992.1

  Methyl α- and β-D-galactopyranosides and 4-O-β-D-galactopyranosyl-3,6-anhydro-L-galactose dimethylacetal were sulfated with sulfuric acid and dicyclohexylcarbodi-imide as a condensation reagent. The sulfated sugars were isolated by ion-exchange chromatography, characterized, and assigned by methylation analyses. On the basis of the yield of each sulfated product that was isolated, sulfation on O-6 appeared to be predominant.

  甲基α-和β-D-半乳糖吡喃苷及4-O-β-D-半乳糖吡喃苷-3,6-去水-L-半乳糖二甲基缩醛在硫酸和二环己基碳二亚胺的作用下进行了硫酸化。硫酸化的糖通过离子交换色谱法分离，进行了表征，并通过甲基化分析进行了鉴定。根据分离出的每种硫酸化产物的产率，O-6上的硫酸化似乎占主导地位。
• Clingman et al., Journal of the Chemical Society, 1957, p. 197,199
  作者：Clingman et al.

  DOI：——

  日期：——
• Studies on the Chemical Constitution of Agar-agar. XVII Isolation of Crystalline Agarobiose Dimethylacetal by Partial Methanolysis of Agar-agar
  作者：Choji Araki、Susumu Hirase

  DOI：10.1246/bcsj.27.109

  日期：1954.2
• Isolation of Agarobiose Derivative from the Mucilage of Gloiopeltis Furcata
  作者：Susumu Hirase、Choji Araki、Toshiya Ito

  DOI：10.1246/bcsj.31.428

  日期：1958.4

  1. The mucilage of Gloiopeltis furcata has been subjected to partial methanolysis, which resulted in the isolation of methyl d-galactoside, 3,6-anhydro-l-galactose dimethylacetal, methyl d-xyloside and agarobiose dimethylacetal.2. Since the agarobiose derivative was obtained in a good yield, it has been concluded that the disaccharide represents the chief repeating unit of the mucilage molecule, if the sulfate residues present in the mucilage are left out of consideration.3. Xylose has been identified for the first place so far as the Gloiopeltis mucilage is concerned. But the yield was so low that the sugar might be possibly derived from a contaminating xylan.

  1. Gloiopeltis furcata 的黏液经过部分甲醇解作用，最终分离出甲基 d-半乳糖苷、3,6-脱水-l-半乳糖二甲基缩醛、甲基 d-木糖苷和琼脂二糖二甲基缩醛。2. 由于琼脂二糖衍生物获得了较好的产率，因此可以断定，该二糖代表了黏液分子的主要重复单元，前提是忽略黏液中存在的硫酸盐残基。3. 目前为止，木糖被首次确认与 Gloiopeltis 的黏液相关。但由于产率极低，该糖可能源自污染的木聚糖。