[(2R,3S,4S,5S,6S)-3,5-Dibenzyloxy-6-methoxy-4-vinyl-tetrahydropyran-2-yl]methyl acetate | 251456-64-1

• 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: [(2R,3S,4S,5S,6S)-3,5-Dibenzyloxy-6-methoxy-4-vinyl-tetrahydropyran-2-yl]methyl acetate
• 英文别名: [(2R,3S,4S,5S,6S)-4-ethenyl-6-methoxy-3,5-bis(phenylmethoxy)oxan-2-yl]methyl acetate
• CAS: 251456-64-1
• 化学式: C₂₅H₃₀O₆
• 分子量: 426.51
• InChiKey: ANCLPDCJLCTPGK-YCXOGWGTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  31
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(2R,3S,4S,5S,6S)-3,5-Dibenzyloxy-6-methoxy-4-vinyl-tetrahydropyran-2-yl]methyl acetate 在 甲醇 、 samarium diiodide 、 臭氧 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 6.75h， 生成 methyl 6-O-acetyl-2,4-di-O-benzyl-3-deoxy-3-C-(1'-(2',3',4',6'-tetra-O-benzyl-1'-deoxy-α-D-mannopyranosyl)(oxythiocarbonylimidazolyl)methyl)-α-D-mannopyranoside
  参考文献：
  名称：

  Application of the Anomeric Samarium Route for the Convergent Synthesis of the C-Linked Trisaccharide α-d-Man-(1→3)-[α-d-Man-(1→6)]-d-Man and the Disaccharides α-d-Man-(1→3)-d-Man and α-d-Man-(1→6)-d-Man

  摘要：

  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.

  DOI：

  10.1021/jo020339z
• 作为产物：
  描述：

  1,6-anhydro-2,4-di-O-benzyl-3-deoxy-3-C-vinyl-β-D-mannopyranose 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 生成 [(2R,3S,4S,5S,6S)-3,5-Dibenzyloxy-6-methoxy-4-vinyl-tetrahydropyran-2-yl]methyl acetate
  参考文献：
  名称：

  Application of the Anomeric Samarium Route for the Convergent Synthesis of the C-Linked Trisaccharide α-d-Man-(1→3)-[α-d-Man-(1→6)]-d-Man and the Disaccharides α-d-Man-(1→3)-d-Man and α-d-Man-(1→6)-d-Man

  摘要：

  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.

  DOI：

  10.1021/jo020339z

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。
• 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。
• [EN] MANNOSE DERIVATIVES FOR TREATING BACTERIAL INFECTIONS<br/>[FR] DÉRIVÉS DE MANNOSE POUR TRAITER LES INFECTIONS BACTÉRIENNES
  申请人：VERTEX PHARMA

  公开号：WO2014055474A1

  公开（公告）日：2014-04-10

  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.