methyl 4-O-methyl-α-D-galactopyranoside | 34698-08-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4-O-methyl-α-D-galactopyranoside
• 英文别名: methyl α-D-galactopyranoside；Methyl 4-O-methyl-α-D-galactopyranosid；Methyl-4-O-methyl-α-D-galactopyranosid；(2S,3R,4R,5R,6R)-6-(hydroxymethyl)-2,5-dimethoxyoxane-3,4-diol
• CAS: 34698-08-3
• 化学式: C₈H₁₆O₆
• 分子量: 208.211
• InChiKey: YEEFEWNECFNTEE-YQXRAVKXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  88.4
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 4-O-methyl-α-D-galactopyranoside 在 吡啶 、 硫酸 、 溶剂黄146 、 zinc(II) chloride 作用下， 以 乙酸酐 、 溶剂黄146 为溶剂， 反应 13.08h， 生成 p-nitrophenyl 2,3,6-tri-O-benzoyl-4-O-methyl-α-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of Monomethyl Derivatives ofP-Nitrophenyl α-D-Gluco, Galacto, and Mannopyranosides and their Hydrolytic Properties Against α-Glycosidases

  摘要：

  All possible monomethyl derivatives of p-nitrophenyl alpha-D-gluco, galacto, and mannopyranosides were synthesized. Hydrolytic activities of alpha-glucosidase (rice), alpha-galactosidases (green coffee bean, Mortierella vinacea, and Aspergillus niger), and alpha-mannosidases (almond and jack bean) against them were elucidated. The 6-O-methyl galactopyranoside and mannopyranoside were hydrolyzed by the M. vinacea alpha-galactosidase and the almond and jack bean alpha-mannosidases, respectively, while these enzymes did not act on the 2-, 3-, and 4-O-methyl derivatives. On the other hand, lice alpha-glucosidase and green coffee bean and A. niger alpha-galactosidases had no hydrolyzing activities at all against the respective four monomethylated substrates.

  DOI：

  10.1080/07328300008544084
• 作为产物：
  描述：

  methyl 2,3,6-tri-O-benzyl-4-O-methyl-α-D-galactopyranoside 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 乙醇 为溶剂， 反应 18.0h， 生成 methyl 4-O-methyl-α-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of Monomethyl Derivatives ofP-Nitrophenyl α-D-Gluco, Galacto, and Mannopyranosides and their Hydrolytic Properties Against α-Glycosidases

  摘要：

  All possible monomethyl derivatives of p-nitrophenyl alpha-D-gluco, galacto, and mannopyranosides were synthesized. Hydrolytic activities of alpha-glucosidase (rice), alpha-galactosidases (green coffee bean, Mortierella vinacea, and Aspergillus niger), and alpha-mannosidases (almond and jack bean) against them were elucidated. The 6-O-methyl galactopyranoside and mannopyranoside were hydrolyzed by the M. vinacea alpha-galactosidase and the almond and jack bean alpha-mannosidases, respectively, while these enzymes did not act on the 2-, 3-, and 4-O-methyl derivatives. On the other hand, lice alpha-glucosidase and green coffee bean and A. niger alpha-galactosidases had no hydrolyzing activities at all against the respective four monomethylated substrates.

  DOI：

  10.1080/07328300008544084

文献信息

• Regioselective methylation of methyl glycopyranosides with diazomethane in the presence of transition-metal chlorides and of boric acid
  作者：Evgeny V. Evtushenko

  DOI：10.1016/s0008-6215(99)00044-0

  日期：1999.3

  Abstract Partial methylation of the methyl pyranosides of a number of pentoses, hexoses, 6-deoxyhexoses, methyl uronates and their methyl ethers with diazomethane in the presence of transition-metal chlorides and boric acid was studied. It was found for methyl glycosides of pentoses and 6-deoxyhexoses that tin(II), antimony(III), and titanium(IV) chlorides as well as boric acid promoted substitution

  摘要研究了在过渡金属氯化物和硼酸存在下，许多戊糖，己糖，6-脱氧己糖，尿酸甲酯及其甲基醚的甲基吡喃糖苷与重氮甲烷的部分甲基化。发现戊糖和6-脱氧己糖的甲基糖苷中锡（II），锑（III）和钛（IV）氯化物以及硼酸主要促进OH-3的取代，但被铈（III）和锌的取代（II）观察到盐主要取代了OH-2。在所有情况下，甲基β-1-鼠李糖吡喃糖苷的甲基化表现出较高的OH-2反应性。在氯化锡（II），锑（III）和铈（III）的存在下，己糖甲基糖苷的甲基化反应主要产生了3-甲基醚。不参与进一步络合的3-甲基醚 积聚高达50-80％的反应混合物（95％至100％的单甲醚馏分）。建议用于许多糖的方便的甲基醚的合成。
• Topological Effects and Binding Modes Operating with Multivalent Iminosugar-Based Glycoclusters and Mannosidases
  作者：Yoan Brissonnet、Carmen Ortiz Mellet、Sandrine Morandat、M. Isabel Garcia Moreno、David Deniaud、Susan E. Matthews、Sébastien Vidal、Sergej Šesták、Karim El Kirat、Sébastien G. Gouin

  DOI：10.1021/ja406931w

  日期：2013.12.11

  could be an alternative strategy in developing therapeutic GM inhibitors not affecting the lysosomal mannosidases. Dynamic light scattering experiments and atomic force microscopy performed with coincubated solutions of the compounds with JBαMan shed light on the multivalent binding mode. The multivalent compounds were shown to promote the formation of JBαMan aggregates with different sizes and shapes

  最近已经探索了多价亚氨基糖的糖苷酶抑制作用。已经报道了由于特定目标的多价性增强亲和力，当实现酶选择性的提高时，这特别有吸引力，但提出了使用此类新型抑制剂操作的结合模式的问题。在这里，我们描述了一组具有特定拓扑结构的四价和八价亚氨基糖探针的开发，并评估了它们对一组糖苷酶的结合亲和力，包括 Jack Bean α-甘露糖苷酶 (JBαMan) 和生物相关的 II 类 α-甘露糖苷酶来自黑腹果蝇属于糖水解酶家族 38，即高尔基体 α-甘露糖苷酶 ManIIb (GM) 和溶酶体 α-甘露糖苷酶 LManII (LM)。对于具有相同化合价的化合物，观察到非常不同的抑制特性，表明亚氨基糖的空间分布对于微调酶抑制活性至关重要。与单价参照物相比，最好的多价化合物对 JBαMan 的抑制效力显着提高了 800 倍，这对于四价配体来说是突出的。该化合物还显示出比 LM 增加了对 GM 的抑制活性和选择性。这
• HAMEDI, SANGSARI FARID;CHASTRETTE, FRANCINE;CHASTRETTE, MAURICE;BLANC, AL+, REC. TRAV. CHIM. PAYS-BAS., 109,(1990) N, C. 15-20
  作者：HAMEDI, SANGSARI FARID、CHASTRETTE, FRANCINE、CHASTRETTE, MAURICE、BLANC, AL+

  DOI：——

  日期：——
• Synthesis of Monomethyl Derivatives of<i>P</i>-Nitrophenyl α-D-Gluco, Galacto, and Mannopyranosides and their Hydrolytic Properties Against α-Glycosidases
  作者：Wataru Hakamata、Toshiyuki Nishio、Reiko Sato、Takahiro Mochizuki、Kazuya Tsuchiya、Maki Yasuda、Tadatake Oku

  DOI：10.1080/07328300008544084

  日期：2000.1

  All possible monomethyl derivatives of p-nitrophenyl alpha-D-gluco, galacto, and mannopyranosides were synthesized. Hydrolytic activities of alpha-glucosidase (rice), alpha-galactosidases (green coffee bean, Mortierella vinacea, and Aspergillus niger), and alpha-mannosidases (almond and jack bean) against them were elucidated. The 6-O-methyl galactopyranoside and mannopyranoside were hydrolyzed by the M. vinacea alpha-galactosidase and the almond and jack bean alpha-mannosidases, respectively, while these enzymes did not act on the 2-, 3-, and 4-O-methyl derivatives. On the other hand, lice alpha-glucosidase and green coffee bean and A. niger alpha-galactosidases had no hydrolyzing activities at all against the respective four monomethylated substrates.