methyl 6-O-methyl-α-D-glucopyranoside | 5155-48-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 6-O-methyl-α-D-glucopyranoside
• 英文别名: Methyl-6-O-methyl-α-D-glucopyranosid；Methyl 6-o-methyl-alpha-d-glucopyranoside；(2S,3R,4S,5S,6R)-2-methoxy-6-(methoxymethyl)oxane-3,4,5-triol
• CAS: 5155-48-6
• 化学式: C₈H₁₆O₆
• 分子量: 208.211
• InChiKey: FJFRHMFVCLTWOW-CBQIKETKSA-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 6-O-methyl-α-D-glucopyranoside 在 氢氧化钾 、 无水碳酸镉 、 硫酸 、 氢溴酸 、 溶剂黄146 作用下， 以 溶剂黄146 为溶剂， 反应 42.67h， 生成
  参考文献：
  名称：

  Na+-Glucose Cotransporter Inhibitors as Antidiabetic Agents. III. Synthesis and Pharmacological Properties of 4'-Dehydroxyphlorizin Derivatives Modified at the OH Groups of the Glucose Moiety.

  摘要：

  为了克服消化道中β-葡萄糖苷酶对4'-去氢氧基根皮苷衍生物（1、2、3）的水解作用，对其葡萄糖部分上的羟基进行了多种模式的修饰，随后评估了这些修饰化合物对大鼠尿糖排泄的影响。其中，三乙酰化（9）、2,3-二乙酰化（17）、6-O-甲氧羰基化（34）、4-O-甲氧羰基化（38）和2-O-乙酰化（41）衍生物通过口服给药（p.o.）显示出比母体化合物2更强的效果。化合物34、38和41对β-葡萄糖苷酶的稳定性高于化合物2。口服活性的增加与对β-葡萄糖苷酶稳定性的增强相关。

  DOI：

  10.1248/cpb.46.1545
• 作为产物：
  描述：

  methyl 2,3,4-tri-O-acetyl-α-D-glucopyranose 生成 methyl 6-O-methyl-α-D-glucopyranoside
  参考文献：
  名称：

  Koizumi, Kyoko; Utamura, Toshiko, Chemical and pharmaceutical bulletin, 1981, vol. 29, # 10, p. 2776 - 2784

  摘要：

  DOI：

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。
• An easy route to methyl 6-O-alkyl glycosides
  作者：Corinne Bayle、Andrée Gadelle

  DOI：10.1016/0040-4039(94)85213-8

  日期：1994.4

  Methyl 6-O-alkyl-glucopyranosides were obtained in excellent yield from methyl 6-deoxy-6-iodoglucopyranoside and the appropriate alcohol in the presence of chlorine.

  6- ø -烷基吡喃葡萄糖苷是在良好的收率由甲基-6-脱氧-6- iodoglucopyranoside和在氯的存在下适当的醇而获得。
• New Method for Regioselective Glycosylation Employing Saccharide Oxyanions
  作者：Martin Matwiejuk、Joachim Thiem

  DOI：10.1002/ejoc.201100861

  日期：2011.10

  As an alternative concept for glycosylation, the prior activation of acceptor hydroxy groups for selective glycosidic bond formation, was investigated to give complex oligosaccharides. Oxyanions obtained from partially protected saccharides were glycosylated by employing glycopyranosyl halides, and the regiochemical results were studied. Initially, partially methylated methyl-α-D-glucopyranosides were

  作为糖基化的替代概念，研究了先激活受体羟基以形成选择性糖苷键，以得到复杂的寡糖。从部分保护的糖类中获得的氧阴离子通过使用吡喃糖基卤化物进行糖基化，并研究了区域化学结果。最初，部分甲基化的甲基-α-D-吡喃葡萄糖苷被用作模型系统来研究碱基促进糖基化的基本机制原理。实现了高区域选择性和立体特异性糖苷键的形成，并且该方法的范围通过不同的全苄化糖基供体进行了扩展。
• A Synthetic Toolbox for the In Situ Formation of Functionalized Homo- and Heteropolysaccharide-Based Hydrogel Libraries
  作者：Nick Dibbert、Andreas Krause、Julio-Cesar Rios-Camacho、Ina Gruh、Andreas Kirschning、Gerald Dräger

  DOI：10.1002/chem.201603748

  日期：2016.12.23

  namely, the adhesion factor cyclic RGD pentapeptide, by using an orthogonal click reaction. This set of modified polysaccharides served to create a library of hydrogels that differ in the combination of polysaccharide strands and the degree of cross‐linking. The different hydrogels were evaluated with respect to their rheological properties, their ability to absorb water, and their cytotoxicity towards

  报道了一种合成工具箱，用于将醛基和肼基基团引入多糖透明质酸，藻酸盐，右旋糖酐，支链淀粉，糖原和羧甲基纤维素中，并将其用于水凝胶形成。混合衍生自同一天然前体的不同功能化多糖后，发生cross交联，从而形成由一种多糖主链组成的水凝胶。同样，混合相应的醛基和酰肼基修饰的多糖后，可以形成基于两条不同多糖链的水凝胶。这些研究的第二条线为通过正交点击反应引入生物医学相关的配体（即粘附因子环状RGD五肽）铺平了道路。这组修饰的多糖用于创建水凝胶库，该库在多糖链的组合和交联度方面有所不同。评价了不同的水凝胶的流变性，吸水能力以及对人成纤维细胞培养的细胞毒性。所研究的水凝胶均无细胞毒性，因此，它们在组织工程中的应用主要具有生物相容性。
• 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.