(5R)-2,6-di-O-benzyl-5-C-methoxy-α-L-ribo-hexopyranosyl-(1->4)-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal | 1215311-28-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (5R)-2,6-di-O-benzyl-5-C-methoxy-α-L-ribo-hexopyranosyl-(1->4)-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal
• CAS: 1215311-28-6
• 化学式: C₃₅H₅₀O₁₃
• 分子量: 678.774
• InChiKey: QGKLBINHLGGOMD-SOMKDEPSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.89
• 重原子数：
  48.0
• 可旋转键数：
  15.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  141.99
• 氢给体数：
  2.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  (5R)-2,6-di-O-benzyl-5-C-methoxy-α-L-ribo-hexopyranosyl-(1->4)-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal 在 水 、 三氟乙酸 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以73%的产率得到2,6-di-O-benzyl-L-ribo-aldohexose-5-ulose
  参考文献：
  名称：

  Lactose as an inexpensive starting material for the preparation of aldohexos-5-uloses: synthesis of l-ribo and d-lyxo derivatives

  摘要：

  Partially protected derivatives of L-ribo- and D-lyxo-aldohexos-5-ulose have been prepared starting from triacetonlactose dimethyl acetal derivatives. Key steps of the synthetic sequences are (a) the synthesis of 4'-deoxy-4'-eno- and 6'-deoxy-5'-eno lactose derivatives, and (b) the epoxidation-methanolysis of the above-mentioned enol ethers to give 1,5-bis-glycopyranosides, masked form of the target 1,5-dicarbonyl hexoses. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.11.027
• 作为产物：
  描述：

  2,6-di-O-benzyl-4-deoxy-α-L-erythro-hex-4-enopyranosyl-(1->4)-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal 在 间氯过氧苯甲酸 作用下， 以 甲醇 为溶剂， 以58%的产率得到(5R)-2,6-di-O-benzyl-5-C-methoxy-α-L-ribo-hexopyranosyl-(1->4)-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal
  参考文献：
  名称：

  Lactose as an inexpensive starting material for the preparation of aldohexos-5-uloses: synthesis of l-ribo and d-lyxo derivatives

  摘要：

  Partially protected derivatives of L-ribo- and D-lyxo-aldohexos-5-ulose have been prepared starting from triacetonlactose dimethyl acetal derivatives. Key steps of the synthetic sequences are (a) the synthesis of 4'-deoxy-4'-eno- and 6'-deoxy-5'-eno lactose derivatives, and (b) the epoxidation-methanolysis of the above-mentioned enol ethers to give 1,5-bis-glycopyranosides, masked form of the target 1,5-dicarbonyl hexoses. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.11.027