2,3,4-tri-O-acetyl-6-deoxy-6-iodo-5-C-methoxy-β-D-galactopyranosyl azide | 692776-40-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2,3,4-tri-O-acetyl-6-deoxy-6-iodo-5-C-methoxy-β-D-galactopyranosyl azide
• 英文别名: [(2S,3R,4R,5R,6R)-3,5-diacetyloxy-6-azido-2-(iodomethyl)-2-methoxyoxan-4-yl] acetate
• CAS: 692776-40-2
• 化学式: C₁₃H₁₈IN₃O₈
• 分子量: 471.206
• InChiKey: ADSGHCZVMLQYPB-SYLRKERUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  112
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  2,3,4-tri-O-acetyl-6-deoxy-6-iodo-β-D-galactopyranosyl azide 在 N-碘代丁二酰亚胺 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 50.0h， 生成 2,3,4-tri-O-acetyl-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