(5R)-3,4-O-isopropylidene-5-C-methoxy-α-L-ribo-hexopyranosyl-(1->4)-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal | 1215311-21-9

• 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: (5R)-3,4-O-isopropylidene-5-C-methoxy-α-L-ribo-hexopyranosyl-(1->4)-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal
• CAS: 1215311-21-9
• 化学式: C₂₄H₄₂O₁₃
• 分子量: 538.59
• InChiKey: GGOUOCWCIRBITD-JEEXWFCDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.23
• 重原子数：
  37.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 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)-3,4-O-isopropylidene-5-C-methoxy-α-L-ribo-hexopyranosyl-(1->4)-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal 、 溴甲苯 在 氢氧化钾 、 18-冠醚-6 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.5h， 以94%的产率得到(5R)-2,6-di-O-benzyl-3,4-O-isopropylidene-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
• 作为产物：
  描述：

  6-deoxy-3,4-O-isopropylidene-α-L-ribo-hex-5-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13%的产率得到(5S)-2,5-anhydro-3,4-O-isopropylidene-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