6-deoxy-6-iodo-5-C-methoxy-β-D-galactopyranosyl azide | 692776-34-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-deoxy-6-iodo-5-C-methoxy-β-D-galactopyranosyl azide
• 英文别名: (2S,3R,4R,5R,6R)-6-azido-2-(iodomethyl)-2-methoxyoxane-3,4,5-triol
• CAS: 692776-34-4
• 化学式: C₇H₁₂IN₃O₅
• 分子量: 345.094
• InChiKey: XRDCGDVUYMQHRJ-NYMZXIIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  93.5
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  6-deoxy-6-iodo-5-C-methoxy-β-D-galactopyranosyl azide 在 palladium dihydroxide 氢气 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以73%的产率得到1,5,6-trideoxy-1,5-imino-D-galactitol
  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：

  2,3,4-tri-O-acetyl-6-deoxy-6-iodo-5-C-methoxy-β-D-galactopyranosyl azide 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以0.168 g的产率得到6-deoxy-6-iodo-5-C-methoxy-β-D-galactopyranosyl 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