methyl 6-deoxy-4-O-tosyl-β-D-gulopyranoside | 315186-11-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 6-deoxy-4-O-tosyl-β-D-gulopyranoside
• CAS: 315186-11-9
• 化学式: C₁₄H₂₀O₇S
• 分子量: 332.375
• InChiKey: PSJDSJJRIOHJCU-RMTQGBGSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.18
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  102.29
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 methyl 6-deoxy-4-O-tosyl-β-D-gulopyranoside 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 、 吡啶 为溶剂， 反应 7.0h， 以45%的产率得到methyl 2,3-di-O-acetyl-4-azido-4,6-dideoxy-β-D-gulopyranoside
  参考文献：
  名称：

  Non-Glycosidic Azides of D-Altro- and D-Gulopyranose

  摘要：

  Starting with methyl 2-O-cyclohexylcarbamoyl-3,4-O-(2,2,2-trichloroethylidene)-alpha -D-altropyranoside side (I), methyl 4-O-cyclohexylcarbamoyl-2,3-O-(2,2,2-trichloroethylidene)-beta -n-gulopyranoside (12), and methyl 6-O-cyclohexylcarbamoyl-2,3-O-(2,2,2-trichloroethylidene)-beta -D-gulopyranoside (21), the 6-azido-6-deoxyaltroses 4, 6, 11, the 6-azido-6-deoxy-D-gulose 14, the 4-azido-4,6-dideoxy-D-gulose 20, and the 4-azido-4-deoxy-D-gulose 26 were synthesised via iodinated or tosylated precursors. Additionally, two gluco-configured azides, the 3-azido-3,6-dideoxy-D-glucose (19) and the 3-azido-3-deoxy-D-glucose (25), were obtained besides the desired 4-azido-4-deoxy-D-gulosides 20 and 26, when methyl 6-deoxy-4-O-tosyl-beta -D-gulopyranoside (18) and methyl 6-O-cyclohexylcarbamoyl-4-O-tosyl-beta -D-gulopyranoside, respectively, were reacted with sodium azide. An X-ray analysis is presented for methyl 2,4-di-O-acetyl-3-azido-3,6-dideoxy-beta -D-glucose (19).

  DOI：

  10.1080/07328300008544131
• 作为产物：
  描述：

  methyl (endo-H)-4-O-(cyclohexylcarbamoyl)-2,3-O-(2,2,2-trichloroethylidene)-β-D-gulopyranoside 在 咪唑 、 偶氮二异丁腈 、 碘 、 三正丁基氢锡 、 sodium methylate 、 三苯基膦 、 三氟乙酸 作用下， 以 吡啶 、 甲醇 、 甲苯 为溶剂， 反应 61.92h， 生成 methyl 6-deoxy-4-O-tosyl-β-D-gulopyranoside
  参考文献：
  名称：

  Non-Glycosidic Azides of D-Altro- and D-Gulopyranose

  摘要：

  Starting with methyl 2-O-cyclohexylcarbamoyl-3,4-O-(2,2,2-trichloroethylidene)-alpha -D-altropyranoside side (I), methyl 4-O-cyclohexylcarbamoyl-2,3-O-(2,2,2-trichloroethylidene)-beta -n-gulopyranoside (12), and methyl 6-O-cyclohexylcarbamoyl-2,3-O-(2,2,2-trichloroethylidene)-beta -D-gulopyranoside (21), the 6-azido-6-deoxyaltroses 4, 6, 11, the 6-azido-6-deoxy-D-gulose 14, the 4-azido-4,6-dideoxy-D-gulose 20, and the 4-azido-4-deoxy-D-gulose 26 were synthesised via iodinated or tosylated precursors. Additionally, two gluco-configured azides, the 3-azido-3,6-dideoxy-D-glucose (19) and the 3-azido-3-deoxy-D-glucose (25), were obtained besides the desired 4-azido-4-deoxy-D-gulosides 20 and 26, when methyl 6-deoxy-4-O-tosyl-beta -D-gulopyranoside (18) and methyl 6-O-cyclohexylcarbamoyl-4-O-tosyl-beta -D-gulopyranoside, respectively, were reacted with sodium azide. An X-ray analysis is presented for methyl 2,4-di-O-acetyl-3-azido-3,6-dideoxy-beta -D-glucose (19).

  DOI：

  10.1080/07328300008544131