methyl α-nigeroside | 68709-26-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl α-nigeroside
• 英文别名: Glc(a1-3)a-Glc1Me；(2R,3R,4S,5S,6R)-2-[(2R,3R,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-methoxyoxan-4-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 68709-26-2
• 化学式: C₁₃H₂₄O₁₁
• 分子量: 356.327
• InChiKey: WOKXHOIRHHAHDA-NYBCVFNSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.6
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  179
• 氢给体数：
  7
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  (2R,3r,4s,5r,6r)-3,4,5-三s(苄氧基)-2-溴-6-(3-苯基丙基)四氢-2H-吡喃 在 palladium on activated charcoal 4 A molecular sieve 、 四乙基溴化铵 、 氢气 作用下， 以 溶剂黄146 为溶剂， 反应 26.0h， 生成 methyl α-nigeroside
  参考文献：
  名称：

  Selective α-d-glucosylation of methyl 4,6-O-benzylidene-α- and β-d-glucopyranosides with 2,3,4,6-tetra-O-benzyl-α-d-glucopyranosyl bromide under catalysis by halide ion

  摘要：

  DOI：

  10.1016/s0008-6215(00)90437-3

文献信息

• Intramolecular Glycosidation by Click Reaction Mediated Spacer Generation Followed by Spacer Cleavage
  作者：Amit Kumar、Yiqun Geng、Richard R. Schmidt

  DOI：10.1002/ejoc.201201076

  日期：2012.12

  glycosidation with N-iodosuccinimide/trifluoromethansulfonic acid as the activating system afforded β-(1–3)- and α-(1–2)-linked disaccharides as part of 14-membered macrocycles. Descriptors for these reactions are proposed that consider the donor and acceptor attachment sites and the stereochemistry of the functional groups. Investigation of the influence of 2-O-linked 1-aryl-1,2,3-triazol-4-ylmethyl

  具有连位羟基的 2-O-炔丙基取代的糖基供体和 O-(2-叠氮基苄基)-取代的受体容易进行点击反应。以 N-碘代琥珀酰亚胺/三氟甲磺酸为激活系统的分子内糖苷化得到 β-(1-3)- 和 α-(1-2)-连接的二糖，作为 14 元大环的一部分。提出了这些反应的描述，考虑供体和受体连接位点以及官能团的立体化学。对包含在间隔基中的 2-O-连接的 1-芳基-1,2,3-三唑-4-基甲基基团对异头异构选择性的影响的研究表明没有嵌合辅助。此外，还表明间隔基团在 Birch 还原条件下很容易裂解。
• N.m.r. and conformational studies of the methyl glycosides of some 1,2- and 1,3-linked disaccharides
  作者：Per-Erik Jansson、Lennart Kenne、Elke Schweda

  DOI：10.1039/p19880002729

  日期：——

  1 H and 13C N.m.r. studies and conformational analysis have been performed on the methyl glycosides of ten 1,2- and 1,3-linked disaccharides in which the glycosidic linkages have different stereochemical surroundings. Conformational analysis, using the HSEA-approach, indicates a number of protonoxygen and proton–proton interactions, resulting, inter alia, in downfield and upfield shifts of anomeric

  1 H和13 C Nmr研究和构象分析已对十个1,2-和1,3-连接的二糖的甲基糖苷进行了研究，其中糖苷键具有不同的立体化学环境。构象分析，使用HSEA的方法中，表示数字protonoxygen和质子-质子相互作用，所得的尤其，在异头质子信号的前冲和高场位移，分别。获得的13 C nmr糖基化位移已用于模拟1,3-连接的α-和β- D-葡聚糖的光谱。
• Formation of α-(1 → 6), α-(1 → 3), and α-(1 → 2) glycosidic linkages by dextransucrase from Streptococcus sanguis in acceptor-dependent reactions
  作者：Mrinal K. Bhattacharjee、Robert M. Mayer

  DOI：10.1016/0008-6215(93)80034-c

  日期：1993.4

  Dextransucrase from Streptococcus sanguis 10558 was found to synthesize alpha-(1 --> 6), alpha-(1 --> 3), and alpha-(1 --> 2) linkages during an acceptor-dependent glucosyl transfer reaction. Normally, new glucosyl residues are added at C-6 of monosaccharide acceptors. However, sugars blocked at C-6 also can serve as good acceptors. The disaccharide and trisaccharide products formed when methyl 6-bromo-6-deoxy-alpha-D-glucopyranoside was used as acceptor were isolated and characterized. Both were found to contain only alpha-(1 --> 3) glycosidic bonds. This supports the hypothesis that when C-6 is blocked the acceptor binds to the enzyme in a flipped orientation, resulting in an approximate exchange in space of the C-3 and C-6, thereby putting C-3 adjacent to the active site. The second alpha-(1 --> 3) links in the trisaccharide are formed by a single-chain mechanism without release of the intermediate disaccharide. With maltose as acceptor, new glucosyl residues are added at C-6'. However, if that position is blocked with a bromine atom, the resulting compound, 6'-bromo-6'-deoxy-maltose, can still serve as an acceptor. The product in this case was isolated and characterized. The new glycosidic link was found to be alpha-(1 --> 2).