methyl 3-O-methyl-α-D-mannopyranoside | 27552-06-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-O-methyl-α-D-mannopyranoside
• 英文别名: (2R,3R,4S,5S,6S)-2-(hydroxymethyl)-4,6-dimethoxyoxane-3,5-diol
• CAS: 27552-06-3
• 化学式: C₈H₁₆O₆
• 分子量: 208.211
• InChiKey: OETRAPPMILRBSS-HEIBUPTGSA-N

物化性质

• 沸点：
  391.1±42.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 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 3-O-methyl-α-D-mannopyranoside 在 盐酸 、 sodium hydride 、 sodium cyanoborohydride 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 9.25h， 生成 methyl 2,6-dibenzyl-3-methyl-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of a hexasaccharide acceptor corresponding to the reducing terminus of mycobacterial 3-O-methylmannose polysaccharide (MMP)

  摘要：

  The title compound methyl O-(2,6-di-O-benzyl-3-O-methyl-alpha-D-mannopyranosyl)-[(1 --> 4)- O-(2,6-di-O-benzyl-3-O-methyl-alpha-D-mannopyranosyl)](4)-(1 --> 4)-2,6-di-O-benzyl-3-O-methyl-alpha-D- mannopyranoside (2) was synthesized in a blockwise manner, employing trichloroacetimidate (11) and (20) as glycosyl donors. The strategy relies on the single-step preparation of the 3-O-methyl ethers (4) and (12) as starting materials. Since all intermediates contain one or more OCH3 groups, they are easily identified by NMR spectroscopy using the methyl proton signals, Compound 2 corresponds to the reducing terminal hexasaccharide of mycobacterial 3-O-methylmannose polysaccharide (MMP). MMP has the unusual property of stimulating the fatty acid synthetase multienzyme complex. Compound 2 can serve as a suitable glycosyl acceptor for the synthesis of extended fragments of MMP. (C) 1996 Elsevier Science-Ltd.

  DOI：

  10.1016/s0008-6215(96)00239-x
• 作为产物：
  描述：

  methyl-4,6-O-phenylmethylene-α-D-mannopyranoside 在 二正丁基氧化锡 、 溶剂黄146 作用下， 反应 16.5h， 生成 methyl 3-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。
• Carbohydrate-Lipid Interactions: Affinities of Methylmannose Polysaccharides for Lipids in Aqueous Solution
  作者：Lan Liu、Yu Bai、Nian Sun、Li Xia、Todd L. Lowary、John S. Klassen

  DOI：10.1002/chem.201201222

  日期：2012.9.17

  the measured affinity of the extracted MMPs for trans‐parinaric acid is two orders of magnitude smaller than the reported value, which was determined by using a fluorescence assay. Using a newly developed competitive binding assay, referred to as the “proxy protein/proxy ligand” ESI‐MS method, it was shown that MMPs bind specifically to NAs in aqueous solution, with apparent affinities of approximately

  之间的相互作用3- Ô甲基-甘露糖多糖蛋白酶（MMPs），从提取的耻垢分枝杆菌（由MMP-10，-11的混合物，-12和-13），或通过化学合成（MMP-5中得到的小号， -通过电喷雾电离质谱法对8 s，-11 s和14 s以及线性饱和和不饱和脂肪酸（FAs）以及环烷酸（NAs）在25°C和pH 8.5的水溶液中的商业混合物进行了定量（ESI-MS）。MMP与四个FA（肉豆蔻酸，棕榈酸，硬脂酸和反式脂肪酸）结合的缔合常数（K a）派瑞纳酸）是通过间接ESI-MS分析（“代理蛋白”方法）进行测量的。所述ķ一个值在10 4 -10 5 中号-1范围，并且基于用于与棕榈酸，增加与碳水化合物的尺寸合成MMP的结合获得的结果。值得注意的是，所提取的MMP对反链烷酸的亲和力比报道的值小两个数量级，后者是通过荧光测定法测定的。使用新开发的竞争性结合测定法，即“代理蛋白质/代理配体” ESI-MS方法，结
• Microscale cleavage reaction of (phenyl)benzyl ethers by ferric chloride
  作者：Myung Hwan Park、Reiji Takeda、Koji Nakanishi

  DOI：10.1016/s0040-4039(00)96395-0

  日期：1987.1

  Anhydrous FeCl3 in CH2Cl2 cleaves benzyl and p-phenylbenzyl ethers of sugars in 15–30 minutes and 2–3 minutes, respectively, at room temperature in >70% yields; methyl ethers and acyl groups are not affected.

  CH 2 Cl 2中的无水FeCl 3在室温下分别在15–30分钟和2–3分钟内裂解糖的苄基和对苯基苄基醚，收率> 70％。甲基醚和酰基不受影响。
• 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.