methyl 2,3,4-tri-O-benzyl-6-O-methyl-α-D-mannopyranoside | 27552-07-4

• 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-tri-O-benzyl-6-O-methyl-α-D-mannopyranoside
• 英文别名: methyl 6-O-methyl-α-D-mannopyranoside；Methyl-6-O-methyl-α-D-mannopyranosid；(2S,3S,4S,5S,6R)-2-methoxy-6-(methoxymethyl)oxane-3,4,5-triol
• CAS: 27552-07-4
• 化学式: C₈H₁₆O₆
• 分子量: 208.211
• InChiKey: FJFRHMFVCLTWOW-HEIBUPTGSA-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 2,3,4-tri-O-benzyl-6-O-methyl-α-D-mannopyranoside 、 乙酸酐 在 硫酸 、 溶剂黄146 作用下， 以3.92 g的产率得到1,2,3,4-tetra-O-acetyl-6-O-methyl-α-D-mannopyranose
  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：

  甲基-D-丙噻 在 palladium on activated charcoal 咪唑 、 氢气 、 四丁基碘化铵 、 sodium hydride 、 氟化氢吡啶 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 25.0~80.0 ℃ 、101.33 kPa 条件下， 反应 39.0h， 生成 methyl 2,3,4-tri-O-benzyl-6-O-methyl-α-D-mannopyranoside
  参考文献：
  名称：

  使用甲基化的单糖分析寡糖甘露糖苷结合蛋白的结合特异性。

  摘要：

  使用特异的O-烷基化单糖和双糖检查了来自Canavalia ensiformis和Dioclea grandiflora的紧密相关凝集素的结合特异性。两种凝集素在单糖C2羟基上接受任何取代。对于C2-O-乙基配体，C2-烷基化的配体-伴刀豆球蛋白A复合物的结合能增加1kcal mol-1，而相应的复合物与Dioclea凝集素的结合能相同。与较早的报道相反，两种凝集素均接受甲基而不是乙基取代C3羟基。根据刀豆球蛋白A结合位点的现有模型来解释结果。虽然结果与伴刀豆球蛋白A延伸结合位点的模型一致，该模型将所有二糖的非还原末端置于单糖结合位点，

  DOI：

  10.1016/s0968-0896(96)00178-2

文献信息

• Methylation of methyl α-d-hexopyranosides with diazo-methane in the presence of a small amount of water
  作者：Yuko Inoue、Kinzo Nagasawa

  DOI：10.1016/0008-6215(87)80024-1

  日期：1987.11

  Abstract The long-time reduction of methyl α- d -gluco-, α- d -manno-, and α- d -galactopyranosides with excess diazomethane-diethyl ether at 25° in the presence of water gave all partially methylated methyl α- d -hexopyranosides which differ in number and position of methyl substitution. The presence of electrolytes, such as potassium or sodium phosphate, in the reaction medium enhanced the degree of methylation

  摘要在水存在下，用过量的重氮甲烷-二乙醚在25°下长时间还原甲基α-d-葡萄糖-，α-d-甘露糖和α-d-吡喃半乳糖苷，所有部分甲基化的甲基α-d -甲基吡喃糖苷的数目和位置不同。反应介质中电解质（例如磷酸钾或磷酸钠）的存在增强了甲基化的程度，从而导致优先形成甲基α-d-己基吡喃糖苷的三-O-甲基衍生物。
• 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。
• A convenient method for the preparation of all of the partially methylated derivatives of methyl α-d-mannopyranoside and α-d-galactopyranoside
  作者：Tomohiro Mega、Atsushi Nishikawa、Tokuji Ikenaka

  DOI：10.1016/0008-6215(83)88296-2

  日期：1983.2
• 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.
• Analysis of the binding specificities of oligomannoside-binding proteins using methylated monosaccharides
  作者：Mary C. Chervenak、Eric J. Toone

  DOI：10.1016/s0968-0896(96)00178-2

  日期：1996.11

  energies of the corresponding complexes with the Dioclea lectin are identical. Both lectins accept methyl, but not ethyl, substitution of the C3 hydroxyl, in contrast to earlier reports. The results are interpreted in terms of existing models of the concanavalin A binding site. While the results are consistent with a model of the concanavalin A extended binding site that places the non-reducing terminus

  使用特异的O-烷基化单糖和双糖检查了来自Canavalia ensiformis和Dioclea grandiflora的紧密相关凝集素的结合特异性。两种凝集素在单糖C2羟基上接受任何取代。对于C2-O-乙基配体，C2-烷基化的配体-伴刀豆球蛋白A复合物的结合能增加1kcal mol-1，而相应的复合物与Dioclea凝集素的结合能相同。与较早的报道相反，两种凝集素均接受甲基而不是乙基取代C3羟基。根据刀豆球蛋白A结合位点的现有模型来解释结果。虽然结果与伴刀豆球蛋白A延伸结合位点的模型一致，该模型将所有二糖的非还原末端置于单糖结合位点，