1,6-anhydro-2,4-di-O-benzyl-3-deoxy-3-C-vinyl-β-D-mannopyranose | 251456-62-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,6-anhydro-2,4-di-O-benzyl-3-deoxy-3-C-vinyl-β-D-mannopyranose
• 英文别名: (1R,2S,3S,4S,5R)-2,4-Dibenzyloxy-3-vinyl-6,8-dioxabicyclo[3.2.1]octane；(1R,2S,3S,4S,5R)-3-ethenyl-2,4-bis(phenylmethoxy)-6,8-dioxabicyclo[3.2.1]octane
• CAS: 251456-62-9
• 化学式: C₂₂H₂₄O₄
• 分子量: 352.43
• InChiKey: DCYQWMHIAGCCEL-LILSUDLASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,6-anhydro-2,4-di-O-benzyl-3-deoxy-3-C-vinyl-β-D-mannopyranose 在 Lindlar's catalyst 2,6-二甲基吡啶 、 喹啉 、 盐酸 、 四丁基氟化铵 、 氢气 、 臭氧 作用下， 以 四氢呋喃 、 甲醇 、 六甲基磷酰三胺 、 二氯甲烷 、 乙酸乙酯 为溶剂， 生成 methyl 2,4-di-O-benzyl-3,6-dideoxy-3,6-di-C-formyl-α-D-mannopyranoside
  参考文献：
  名称：

  A highly convergent synthesis of a branched C-trisaccharide employing a double SmI2-promoted C-glycosylation

  摘要：

  通过 SmI2- 介导的两个甘露糖基吡啶砜单元与单糖二醛的偶联，合成了 α-D-Man-(1→3)-[α-D-Man-(1→6)]- D-Man 的支链 C 三糖类似物。这种方法代表了一种 C-寡糖的高度聚合合成。

  DOI：

  10.1039/b007117j
• 作为产物：
  描述：

  3,7,9-三氧杂三环[4.2.1.02,4]壬烷-5-醇 在 四丁基碘化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 1,6-anhydro-2,4-di-O-benzyl-3-deoxy-3-C-vinyl-β-D-mannopyranose
  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。
• A highly convergent synthesis of a branched C-trisaccharide employing a double SmI2-promoted C-glycosylation
  作者：Lise Munch Mikkelsen、Sussie Lerche Krintel、Troels Skrydstrup、Jesús Jiménez-Barbero

  DOI：10.1039/b007117j

  日期：——

  The branched C-trisaccharide analogue of α-D-Man-(1→3)-[α-D-Man-(1→6)]- D-Man has been synthesised by the SmI2-mediated coupling of two mannosyl pyridyl sulfone units to a monosaccharide dialdehyde. This approach represents a highly convergent synthesis of a C-oligosaccharide.

  通过 SmI2- 介导的两个甘露糖基吡啶砜单元与单糖二醛的偶联，合成了 α-D-Man-(1→3)-[α-D-Man-(1→6)]- D-Man 的支链 C 三糖类似物。这种方法代表了一种 C-寡糖的高度聚合合成。
• MANNOSE DERIVATIVES FOR TREATING BACTERIAL INFECTIONS
  申请人：Vertex Pharmaceuticals Incorporated

  公开号：US20140107049A1

  公开（公告）日：2014-04-17

  The present invention relates to compounds useful for the treatment or prevention of bacteria infections. The invention also provides pharmaceutically acceptable compositions containing the compounds and methods of using the compositions in the treatment of bacteria infections. The invention also provides processes for making the compounds of the invention. The compounds of the present invention are represented by the following structure of Formula A: wherein the variables are as described herein.

  本发明涉及用于治疗或预防细菌感染的化合物。本发明还提供含有该化合物的药学上可接受的组合物以及使用该组合物治疗细菌感染的方法。本发明还提供制备本发明化合物的方法。本发明的化合物由以下A式结构表示：其中变量如本文所述。
• 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.