5-O-benzyl-1,2:3,4-di-O-isopropylidene-α-D-glucoseptanose | 374905-65-4

• 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: 5-O-benzyl-1,2:3,4-di-O-isopropylidene-α-D-glucoseptanose
• 英文别名: (1S,2R,6R,9R,10R)-4,4,12,12-tetramethyl-9-phenylmethoxy-3,5,7,11,13-pentaoxatricyclo[8.3.0.02,6]tridecane
• CAS: 374905-65-4
• 化学式: C₁₉H₂₆O₆
• 分子量: 350.412
• InChiKey: VXLBGMNPUWLRPG-NQNKBUKLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-O-benzyl-1,2:3,4-di-O-isopropylidene-α-D-glucoseptanose 在 吡啶 、 盐酸 、 sodium benzoate 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 77.0h， 生成 3,4-anhydro-5-O-benzyl-1,2-O-isopropylidene-α-D-galactoseptanose
  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
• 作为产物：
  描述：

  1,2:3,4-di-O-isopropylidene-α-D-glucoseptanose 、 氯化苄 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以91%的产率得到5-O-benzyl-1,2:3,4-di-O-isopropylidene-α-D-glucoseptanose
  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

文献信息

• Preparation of 1,2-O-isopropylidene derivatives of α-d-galactoseptanose, β-l-altroseptanose, and 3-O-methyl-α-d-guloseptanose
  作者：Graham E Driver、John D Stevens

  DOI：10.1016/s0008-6215(01)00179-3

  日期：2001.8

  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.