4,5-di-O-acetyl-1,2-O-isopopylidene-3-O-methyl-α-D-guloseptanose | 58024-14-9

• 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: 4,5-di-O-acetyl-1,2-O-isopopylidene-3-O-methyl-α-D-guloseptanose
• 英文别名: 4,5-Di-O-acetyl-1,2-O-isopropyliden-3-O-methyl-α-D-guloseptanose；4,5-Di-O-acetyl-1,2-o-isopropyliden-3-O-methyl-α-D-guloheptanose；[(3aR,6R,7S,8R,8aR)-7-acetyloxy-8-methoxy-2,2-dimethyl-3a,5,6,7,8,8a-hexahydro-[1,3]dioxolo[4,5-b]oxepin-6-yl] acetate
• CAS: 58024-14-9
• 化学式: C₁₄H₂₂O₈
• 分子量: 318.324
• InChiKey: JIMSHEJOIMFMGE-NZEXEKPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  89.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  5-O-benzyl-1,2-O-isopropylidene-3-O-methyl-α-D-glucoseptanose 在 palladium on activated charcoal 吡啶 、 氢气 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 4,5-di-O-acetyl-1,2-O-isopopylidene-3-O-methyl-α-D-guloseptanose
  参考文献：
  名称：

  Preparation of 1,2-O-isopropylidene derivatives of α-d-galactoseptanose, β-l-altroseptanose, and 3-O-methyl-α-d-guloseptanose

  摘要：

  Displacement of the tosyloxy group in 5-O-benzyl-1,2-O-isopropylidene-4-O-(p-toluenesulfonyl)-alpha -D-glucoseptanose has yielded derivatives of 1,2-O-isopropylidene-alpha -D-galactoseptanose. Acid catalysed acetonation then gave 1,2:3,4-di-O-isopropylidene-alpha -D-galactoseptanose or 1,2;4,5-di-O-isopropylidene-alpha -D-galactoseptanose using lower acid concentrations. Reduction of the ketone derived from 1,2:3,4-O-isopropylidene-alpha -D-septanose gave 1,2;3,4-di-O-isopropylidene-beta -L-altroseptanose. Reaction of 3,4-anhydro-5-O-benzyl-1,2-O-isopropylidene-alpha -D-galactoseptanose with sodium methoxide gave 5-0-benzyl-1,2-O-isopropylidene-4-O-methyl-alpha -D-glucoseptanose and 5-0-benzyl-1,2-O-isopropylidene-3-O-methyl-alpha -D-guloseptanose. Solution-state conformations of these compounds have been deduced from their H-1 NMR spectra. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(01)00179-3