5-C-methoxy-β-L-gulopyranosyl azide | 376358-67-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-C-methoxy-β-L-gulopyranosyl azide
• CAS: 376358-67-7
• 化学式: C₇H₁₃N₃O₆
• 分子量: 235.197
• InChiKey: BSUKVBZSYZGQCG-JAIWFUSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.93
• 重原子数：
  16.0
• 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：
  148.14
• 氢给体数：
  4.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  5-C-methoxy-β-L-gulopyranosyl azide 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以23%的产率得到1-脱氧甘露伊霉素
  参考文献：
  名称：

  A General Synthesis of Iminosugars

  摘要：

  1-Deoxynojirimycin, 1-deoxymannojirimycin, and 1-deoxygalactostatin have been synthesized by epoxidation of tri-O-acetyl-6-deoxyhex-5-enopyranosyI azides followed by methanolysis, deacetylation, and catalytic hydrogenation. 1,6-Dideoxygalactostatin was obtained by the reaction of 2,3,4-tri-O-acetyl-6-deoxy-beta-L-arabino-hex-5-enopyranosyl azide with NIS in methanol followed by deacetylation and catalytic hydrogenation. The overall yields were 4.4-23.5% over seven to nine steps.

  DOI：

  10.1021/jo035763u
• 作为产物：
  描述：

  2,3,6-tri-O-acetyl-5-C-methoxy-β-L-gulopyranosyl azide 在 sodium 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 5-C-methoxy-β-L-gulopyranosyl azide
  参考文献：
  名称：

  A General Synthesis of Iminosugars

  摘要：

  1-Deoxynojirimycin, 1-deoxymannojirimycin, and 1-deoxygalactostatin have been synthesized by epoxidation of tri-O-acetyl-6-deoxyhex-5-enopyranosyI azides followed by methanolysis, deacetylation, and catalytic hydrogenation. 1,6-Dideoxygalactostatin was obtained by the reaction of 2,3,4-tri-O-acetyl-6-deoxy-beta-L-arabino-hex-5-enopyranosyl azide with NIS in methanol followed by deacetylation and catalytic hydrogenation. The overall yields were 4.4-23.5% over seven to nine steps.

  DOI：

  10.1021/jo035763u