(Tribenzyl-α-L-fucopyranosyl)allene | 138061-55-9

• 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: (Tribenzyl-α-L-fucopyranosyl)allene
• 英文别名: (2S,3R,4R,5R,6S)-2-methyl-3,4,5-tris(phenylmethoxy)-6-propa-1,2-dienyloxane
• CAS: 138061-55-9
• 化学式: C₃₀H₃₂O₄
• 分子量: 456.582
• InChiKey: CNINSBHRDRNXAH-DKIMQPOESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.87
• 重原子数：
  34.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (Tribenzyl-α-L-fucopyranosyl)allene 在 sodium tetrahydroborate 、 二甲基硫 、 sodium acetate 、 臭氧 作用下， 反应 0.18h， 生成 2,6-anhydro-3,4,5-tri-O-benzyl-7-deoxy-aldehydo-L-glycero-D-gluco-heptose
  参考文献：
  名称：

  Preferred conformation of C-glycosides. 10. Synthesis and conformational analysis of carbon trisaccharides

  摘要：

  A flexible and efficient synthesis of the carbon trisaccharide 2 related to the Type II O(H) blood group determinant has been developed. This route was applied to the synthesis of the trisaccharides 3, 4, and 5. The preferred solution conformations of compounds 2-5 were determined on the basis of vicinal coupling constants in the H-1 NMR spectrum. Each of the four trisaccharides adopts a distinct and well-defined solution conformation in accord with the predictions made on the basis of the preference of the C-glycosidic bond for the ''exo-anomeric'' conformation and the analysis of 1,3-diaxial-like interactions around the C-aglyconic bond.

  DOI：

  10.1021/jo00028a019
• 作为产物：
  描述：

  (3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-ol 在 三氟甲磺酸三甲基硅酯 、 三乙胺 作用下， 以 乙醚 、 乙腈 为溶剂， 生成 (Tribenzyl-α-L-fucopyranosyl)allene
  参考文献：
  名称：

  Preferred conformation of C-glycosides. 10. Synthesis and conformational analysis of carbon trisaccharides

  摘要：

  A flexible and efficient synthesis of the carbon trisaccharide 2 related to the Type II O(H) blood group determinant has been developed. This route was applied to the synthesis of the trisaccharides 3, 4, and 5. The preferred solution conformations of compounds 2-5 were determined on the basis of vicinal coupling constants in the H-1 NMR spectrum. Each of the four trisaccharides adopts a distinct and well-defined solution conformation in accord with the predictions made on the basis of the preference of the C-glycosidic bond for the ''exo-anomeric'' conformation and the analysis of 1,3-diaxial-like interactions around the C-aglyconic bond.

  DOI：

  10.1021/jo00028a019