4,8-anhydro-6,7,9-tri-O-benzyl-1,2,3-trideoxy-4ξ-D-galacto-nonitol | 944725-85-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4,8-anhydro-6,7,9-tri-O-benzyl-1,2,3-trideoxy-4ξ-D-galacto-nonitol
• CAS: 944725-85-3
• 化学式: C₃₀H₃₆O₅
• 分子量: 476.613
• InChiKey: JFZVXMDRNLSHKJ-LYQCGEJCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  35.0
• 可旋转键数：
  12.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  57.15
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4,8-anhydro-6,7,9-tri-O-benzyl-1,2,3-trideoxy-4ξ-D-galacto-nonitol 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 生成 (2R,3R,4R,5R)-2-(hydroxymethyl)-6-propyloxane-3,4,5-triol
  参考文献：
  名称：

  The exo-deoxoanomeric effect in the conformational preferences of C-glycosides

  摘要：

  Rotational studies of a series of beta-D-C-glycopyranosides were carried out by CD and NMR spectroscopy. The populations around the C-glycosidic bond were strongly dependent on the structure of the C-aglycon, the exo-syn rotamer population increasing with the degree of substitution on the C-aglycon. The hydroxymethyl group populations also showed dependence on the aglycon, although to a lesser degree; its gt rotamer smoothly increases with the substitution on the aglycon. These rotational preferences, together with the experimentally observed correlations between H-1 and C-13 NMR chemical shifts and the structural nature of the C-aglycon, point to a stercoelectronic sigma(CH)-sigma*(CO) effect (hyperconjugation) directly involved in the rotation around the pseudo-glycosidic bond and indirectly around the C5-C6 bond (hydroxymethyl group). (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.04.007
• 作为产物：
  描述：

  3,4,6-三邻苄基半乳醛 在 二甲基二环氧乙烷 作用下， 以 乙醚 、 二氯甲烷 、 丙酮 为溶剂， 反应 0.5h， 生成 4,8-anhydro-6,7,9-tri-O-benzyl-1,2,3-trideoxy-4ξ-D-galacto-nonitol
  参考文献：
  名称：

  The exo-deoxoanomeric effect in the conformational preferences of C-glycosides

  摘要：

  Rotational studies of a series of beta-D-C-glycopyranosides were carried out by CD and NMR spectroscopy. The populations around the C-glycosidic bond were strongly dependent on the structure of the C-aglycon, the exo-syn rotamer population increasing with the degree of substitution on the C-aglycon. The hydroxymethyl group populations also showed dependence on the aglycon, although to a lesser degree; its gt rotamer smoothly increases with the substitution on the aglycon. These rotational preferences, together with the experimentally observed correlations between H-1 and C-13 NMR chemical shifts and the structural nature of the C-aglycon, point to a stercoelectronic sigma(CH)-sigma*(CO) effect (hyperconjugation) directly involved in the rotation around the pseudo-glycosidic bond and indirectly around the C5-C6 bond (hydroxymethyl group). (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.04.007