methyl 3-deoxy-3-C-[(α-D-mannopyranosyl)methyl]-α-D-mannopyranoside | 485403-01-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-deoxy-3-C-[(α-D-mannopyranosyl)methyl]-α-D-mannopyranoside
• 英文别名: 7；α-D-Manp-(1→3)-α-D-ManpOMe (methyl 3-deoxy-3-C-[(α-D-mannopyranosyl)methyl])-α-D-mannopyranoside；(2R,3S,4R,5S,6R)-2-[[(2R,3S,4S,5S,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-methoxyoxan-4-yl]methyl]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 485403-01-8
• 化学式: C₁₄H₂₆O₁₀
• 分子量: 354.354
• InChiKey: NMECNZIHXHEXSB-ARFXBCIRSA-N

物化性质

• 沸点：
  653.8±55.0 °C(Predicted)
• 密度：
  1.54±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3
• 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：
  169
• 氢给体数：
  7
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 methyl 3-deoxy-3-C-[(α-D-mannopyranosyl)methyl]-α-D-mannopyranoside 在 吡啶 作用下， 以80 mg的产率得到methyl 3-deoxy-3-C-[(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)methyl]-2,4,6-tri-O-acetyl-α-L-mannopyranoside
  参考文献：
  名称：

  Stereoselective preparation of four 3-C-mannosylated d- and l-glucals from a single starting compound

  摘要：

  The corresponding oxadiene, prepared from the starting perbenzylated alpha-D-mannopyranosylethanal was subjected to stereoselective cycloaddition reactions with R and S methyl (ethenyloxy)(phenyl)acetates. From the two obtained diastereoisomeric cycloadducts, 3-C-alpha-D-mannosylated 1,2-D-glucal and 3-C-alpha-D-mannosylated 1,2-L-glucal were prepared. A simple epimerisation of the starting alpha-D-mannopyranosylethanal afforded perbenzylated beta-D-mannopyranosylethanal, which was converted to 3-C-beta-D-mannosylated 1,2-D-glucal or to 3-C-beta-D-mannosylated 1,2-L-glucal by the same procedure. The structure of the obtained 3-C-alpha-D-mannosylated 1,2-D-glucal has been confirmed independently by its transformation to the known peracetylated methyl alpha-C-(1 -> 3)-mannobioside. The prepared glucals are suitable precursors for the synthesis of stable glycoconjugates with non-hydrolyzable mannose-containing epitopes. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.04.044
• 作为产物：
  描述：

  3,7,9-三氧杂三环[4.2.1.02,4]壬烷-5-醇 在 palladium on activated charcoal samarium diiodide 、 偶氮二异丁腈 、 五氟苯酚 、 三苯基氢化锡 、 氢气 、 sodium methylate 、 四丁基碘化铵 、 sodium hydride 、 臭氧 、 三苯基膦 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 0.5h， 生成 methyl 3-deoxy-3-C-[(α-D-mannopyranosyl)methyl]-α-D-mannopyranoside
  参考文献：
  名称：

  通过SmI 2促进的C-糖基化聚合合成α - C -1,3-甘露糖苷

  摘要：

  所述Ç α-1,3-mannobioside的-disaccharide合成了通过甘露糖吡啶基砜和直接耦合Ç甲酰基支链与所述一个电子还原剂，SMI糖2。使用我们先前描述的脱氧条件，成功除去了在该偶联反应中获得的位阻醇。

  DOI：

  10.1016/s0040-4039(99)01604-4

文献信息

• A convergent synthesis of α-C-1,3-mannobioside via SmI2-promoted C-glycosylation
  作者：Sussie L Krintel、Jesús Jiménez-Barbero、Troels Skrydstrup

  DOI：10.1016/s0040-4039(99)01604-4

  日期：1999.10

  The C-disaccharide of α-1,3-mannobioside has been synthesized via the direct coupling of a mannosyl pyridyl sulfone and a C-formyl branched sugar with the one electron reducing agent, SmI2. The sterically hindered alcohol obtained in this coupling was successfully removed employing our previously described deoxygenating conditions.

  所述Ç α-1,3-mannobioside的-disaccharide合成了通过甘露糖吡啶基砜和直接耦合Ç甲酰基支链与所述一个电子还原剂，SMI糖2。使用我们先前描述的脱氧条件，成功除去了在该偶联反应中获得的位阻醇。
• Application of the Anomeric Samarium Route for the Convergent Synthesis of the <i>C</i>-Linked Trisaccharide α-<scp>d</scp>-Man-(1→3)-[α-<scp>d</scp>-Man-(1→6)]-<scp>d</scp>-Man and the Disaccharides α-<scp>d</scp>-Man-(1→3)-<scp>d</scp>-Man and α-<scp>d</scp>-Man-(1→6)-<scp>d</scp>-Man
  作者：Lise Munch Mikkelsen、Sussie Lerche Krintel、Jesús Jiménez-Barbero、Troels Skrydstrup

  DOI：10.1021/jo020339z

  日期：2002.9.1

  Studies are reported on the assembly of the branched C-trisaccharide, alpha-D-Man-(1-->3)-[alpha-D-Man-(1-->6)]-D-Man, representing the core region of the asparagine-linked oligosaccharides. The key step in this synthesis uses a SmI2-mediated coupling of two mannosylpyridyl sulfones to a C3,C6-diformyl branched monosaccharide unit, thereby assembling all three sugar units in one reaction and with complete stereocontrol at the two anomeric carbon centers. Subsequent tin hydride-based deoxygenation followed by a deprotection step produces the target C-trimer. In contrast to many of the other C-glycosylation methods, this approach employes intact carbohydrate units as C-glycosyl donors and acceptors, which in many instances parallels the well-studied O-glycosylation reactions. The synthesis of the C-disaccharides alpha-D-Man-(1-->3)-D-Man and alpha-D-Man-(1-->6)-D-Man is also described, they being necessary for the following conformational studies of all three carbohydrate analogues both in solution and bound to several mannose-binding proteins.
• Stereoselective preparation of four 3-C-mannosylated d- and l-glucals from a single starting compound
  作者：Zuzana Lövyova、Kamil Parkan、Ladislav Kniežo

  DOI：10.1016/j.tet.2011.04.044

  日期：2011.7

  The corresponding oxadiene, prepared from the starting perbenzylated alpha-D-mannopyranosylethanal was subjected to stereoselective cycloaddition reactions with R and S methyl (ethenyloxy)(phenyl)acetates. From the two obtained diastereoisomeric cycloadducts, 3-C-alpha-D-mannosylated 1,2-D-glucal and 3-C-alpha-D-mannosylated 1,2-L-glucal were prepared. A simple epimerisation of the starting alpha-D-mannopyranosylethanal afforded perbenzylated beta-D-mannopyranosylethanal, which was converted to 3-C-beta-D-mannosylated 1,2-D-glucal or to 3-C-beta-D-mannosylated 1,2-L-glucal by the same procedure. The structure of the obtained 3-C-alpha-D-mannosylated 1,2-D-glucal has been confirmed independently by its transformation to the known peracetylated methyl alpha-C-(1 -> 3)-mannobioside. The prepared glucals are suitable precursors for the synthesis of stable glycoconjugates with non-hydrolyzable mannose-containing epitopes. (C) 2011 Elsevier Ltd. All rights reserved.