methyl 5-C-methoxy-β-D-gulopyranoside | 216577-88-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 5-C-methoxy-β-D-gulopyranoside
• CAS: 216577-88-7
• 化学式: C₈H₁₆O₇
• 分子量: 224.211
• InChiKey: XSLCRAOLQBOCQI-SLBCVNJHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.59
• 重原子数：
  15.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  108.61
• 氢给体数：
  4.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  methyl 5-C-methoxy-β-D-gulopyranoside 在 三氟乙酸 作用下， 以 水 、 乙腈 为溶剂， 反应 0.67h， 以100%的产率得到L-lyxo-hexos-5-ulose
  参考文献：
  名称：

  Preparation of L-Lyxo-Hexos-5-Ulose Through C-3 Epimerization of Bis-Glycopyranosides of L-Arabino-Hexos-5-Ulose¹

  摘要：

  The unreported title compound and its 2,6-di-O-benzyl derivative have been prepared from methyl beta-D-galactopyranoside through a sequence involving the bis-glycoside methyl 2,6-di-O-benzyl-5-C-methoxy-beta-D-galactopyranoside 8, the precursor of L-arabino-hexos-5-ulose, that was converted to the L-lyxo series by inversion at C-3. The inversion was achieved in acceptable yields by selective triflation, followed by displacement with benzoate, and by an oxidation/reduction sequence. Whereas 2,5-di-O-benzyl-L-lyxo-hexos-5-ulose exists entirely as a mixture of the two anomeric 1,4-furanosic forms, the unprotected hexos-5-ulose involves at equilibrium in CD3CN/D2O at least eight tautomers, one of which is predominant.

  DOI：

  10.1080/07328309808001891
• 作为产物：
  描述：

  methyl 2,6-di-O-benzyl-5-C-methoxy-β-D-galactopyranoside 在 palladium on activated charcoal sodium tetrahydroborate 、 四丙基高钌酸铵 、 4 A molecular sieve 、 氢气 、 对甲苯磺酸 、 原乙酸三乙酯 、 N-甲基吗啉氧化物 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 5.0h， 生成 methyl 5-C-methoxy-β-D-gulopyranoside
  参考文献：
  名称：

  Preparation of L-Lyxo-Hexos-5-Ulose Through C-3 Epimerization of Bis-Glycopyranosides of L-Arabino-Hexos-5-Ulose¹

  摘要：

  The unreported title compound and its 2,6-di-O-benzyl derivative have been prepared from methyl beta-D-galactopyranoside through a sequence involving the bis-glycoside methyl 2,6-di-O-benzyl-5-C-methoxy-beta-D-galactopyranoside 8, the precursor of L-arabino-hexos-5-ulose, that was converted to the L-lyxo series by inversion at C-3. The inversion was achieved in acceptable yields by selective triflation, followed by displacement with benzoate, and by an oxidation/reduction sequence. Whereas 2,5-di-O-benzyl-L-lyxo-hexos-5-ulose exists entirely as a mixture of the two anomeric 1,4-furanosic forms, the unprotected hexos-5-ulose involves at equilibrium in CD3CN/D2O at least eight tautomers, one of which is predominant.

  DOI：

  10.1080/07328309808001891