(3aR,5R,6S,7S,7aR)-5-Hydroxymethyl-2-(4-methoxy-phenyl)-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6,7-diol | 790672-73-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: (3aR,5R,6S,7S,7aR)-5-Hydroxymethyl-2-(4-methoxy-phenyl)-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6,7-diol
• CAS: 790672-73-0
• 化学式: C₁₄H₁₈O₇
• 分子量: 298.293
• InChiKey: IAVUSRYSGOMQGC-ZGIFUDTASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.45
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  97.61
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (3aR,5R,6S,7S,7aR)-5-Hydroxymethyl-2-(4-methoxy-phenyl)-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6,7-diol 在 吡啶 作用下， 生成 Acetic acid (2S,3aR,5R,6R,7S,7aR)-6-acetoxy-5-acetoxymethyl-2-(4-methoxy-phenyl)-tetrahydro-[1,3]dioxolo[4,5-b]pyran-7-yl ester 、 Acetic acid (2R,3aR,5R,6R,7S,7aR)-6-acetoxy-5-acetoxymethyl-2-(4-methoxy-phenyl)-tetrahydro-[1,3]dioxolo[4,5-b]pyran-7-yl ester
  参考文献：
  名称：

  Practical Synthesis of 1,2‐O‐Benzylidene and 1,2‐O‐p‐Methoxybenzylidene Hexopyranoses

  摘要：

  An improved and practical synthesis of 1,2-O-benzylidene and 1,2-O-p-methoxybenzylidene hexopyranoses as useful synthons in carbohydrate chemistry is described. The reaction of 2-benzoyloxyglycosyl bromide with sodium borohydride using excess amount of potassium iodide proceeded smoothly to give the corresponding 1,2-O-benzylidene derivative in good yields.

  DOI：

  10.1081/car-120020483
• 作为产物：
  描述：

  3,4,6-tri-O-p-methoxybenzoyl-1,2-O-p-methoxybenzylidene-α-D-glucopyranose 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以100%的产率得到(3aR,5R,6S,7S,7aR)-5-Hydroxymethyl-2-(4-methoxy-phenyl)-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6,7-diol
  参考文献：
  名称：

  Reductive Ring‐Opening Reaction of 1,2‐O‐Benzylidene and 1,2‐O‐p‐Methoxybenzylidene‐α‐D‐glucopyranose Using Diisobutyl Aluminum Hydride

  摘要：

  Regioselectivity in the reductive ring-opening reaction of 3,4,6-tri-O-benzyl-1,2-O-benzylidene and 3,4,6-tri-O-benzyl-1,2-O-p-methoxybenzylidene-alpha-D-glucopyranose using diisobutyl aluminum hydride (DIBAH) was examined. The ratio of the 1-O- and 2-O-p-methoxybenzyl ethers, which were generated from endo-type 1,2-O-p-methoxybenzylidene, was variable by the change of solvent.

  DOI：

  10.1081/car-200030087