methyl 2-O-cyclohexylcarbamoyl-6-deoxy-3,4-O-ethylidene-6-iodo-α-D-altropyranoside | 315185-83-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-O-cyclohexylcarbamoyl-6-deoxy-3,4-O-ethylidene-6-iodo-α-D-altropyranoside
• CAS: 315185-83-2
• 化学式: C₁₆H₂₆INO₆
• 分子量: 455.29
• InChiKey: MAXFJWYRUMDBNL-BBSLFKGGSA-N

反应信息

• 作为反应物：
  描述：

  methyl 2-O-cyclohexylcarbamoyl-6-deoxy-3,4-O-ethylidene-6-iodo-α-D-altropyranoside 在 吡啶 、 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 11.5h， 生成 methyl 2-O-acetyl-6-azido-6-deoxy-3,4-O-ethylidene-α-D-altropyranoside
  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 2-O-cyclohexylcarbamoyl-3,4-O-ethylidene-α-D-altropyranoside 在 咪唑 、 碘 、 三苯基膦 作用下， 以 甲苯 为溶剂， 反应 0.33h， 以98%的产率得到methyl 2-O-cyclohexylcarbamoyl-6-deoxy-3,4-O-ethylidene-6-iodo-α-D-altropyranoside
  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