3,6-anhydro-5-azido-5-deoxy-3-C-ethoxycarbonylmethyl-1,2-O-isopropylidene-α-D-glucofuranose | 188249-17-4

• 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: 3,6-anhydro-5-azido-5-deoxy-3-C-ethoxycarbonylmethyl-1,2-O-isopropylidene-α-D-glucofuranose
• 英文别名: ethyl 2-[(1S,2R,6R,8R,9R)-9-azido-4,4-dimethyl-3,5,7,11-tetraoxatricyclo[6.3.0.02,6]undecan-1-yl]acetate
• CAS: 188249-17-4
• 化学式: C₁₃H₁₉N₃O₆
• 分子量: 313.31
• InChiKey: RKPOTJJQVMAYKD-HQHREHCSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  77.6
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3,6-anhydro-5-azido-5-deoxy-3-C-ethoxycarbonylmethyl-1,2-O-isopropylidene-α-D-glucofuranose 在 palladium hydroxide - carbon Amberlite IR 120 (H⁺) resin 、 氢气 作用下， 以 水 、 乙醇 为溶剂， 20.0~40.0 ℃ 、344.74 kPa 条件下， 反应 31.5h， 以24.4%的产率得到3,6-anhydro-1-deoxy-3-C-ethoxycarbonylmethylnojirimycin
  参考文献：
  名称：

  Synthesis and Reactions of 3-C-Branched-Chain Analogues of 3,6-Anhydrodeoxynojirimycin

  摘要：

  The syntheses of 3,6-anhydro-1-deoxy-3-C-ethoxycarbonylmethyl- (4) and 3-C-(2-hydroxyethyl)nojirimycin (5) from 5-azido-6-O-tert-butyldiphenylsiyl-5-deoxy-1,2-O-isopropylidene-alpha-D-glucofuranose (8) are described. The key intermediate is 5-azido-6-O-tert-butyldiphenylsilyl-3,5-dideoxy-3-C-ethoxycarbonylmethylene-1,2-O-isopropylidene-alpha-D-ribo-hex-3-enofuranose (11) which was obtained by condensation of 5-azido-6-O-tertbutyldiphenylsilyl-5-deoxy- 1,2-O-isopropylidene-alpha-D-ribo-hexos-3-ulofuranose (10) with (ethoxycarbonylmethylene)triphenylphosphorane. Conventional benzoylation of 4 resulted in the formation of the lactones 13a and 13b. The 3-C-(2-hydroxyethyl) analogue (5) was synthesized by lithium aluminum hydride reduction of 3,6-anhydroxy-5-azido-5-deoxy-3-C-ethoxycarbonylmethyl- 1,2-O-isopropylidene-alpha-D-glucofuranose (12), followed by deacetalation, and hydrogenation.

  DOI：

  10.1080/07328309708006509
• 作为产物：
  描述：

  5-azido-6-O-tert-butyldiphenylsilyl-3,5-dideoxy-3-C-ethoxycarbonylmethylene-1,2-O-isopropylidene-α-D-ribo-hex-3-enofuranose 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以78.8%的产率得到3,6-anhydro-5-azido-5-deoxy-3-C-ethoxycarbonylmethyl-1,2-O-isopropylidene-α-D-glucofuranose
  参考文献：
  名称：

  Synthesis and Reactions of 3-C-Branched-Chain Analogues of 3,6-Anhydrodeoxynojirimycin

  摘要：

  The syntheses of 3,6-anhydro-1-deoxy-3-C-ethoxycarbonylmethyl- (4) and 3-C-(2-hydroxyethyl)nojirimycin (5) from 5-azido-6-O-tert-butyldiphenylsiyl-5-deoxy-1,2-O-isopropylidene-alpha-D-glucofuranose (8) are described. The key intermediate is 5-azido-6-O-tert-butyldiphenylsilyl-3,5-dideoxy-3-C-ethoxycarbonylmethylene-1,2-O-isopropylidene-alpha-D-ribo-hex-3-enofuranose (11) which was obtained by condensation of 5-azido-6-O-tertbutyldiphenylsilyl-5-deoxy- 1,2-O-isopropylidene-alpha-D-ribo-hexos-3-ulofuranose (10) with (ethoxycarbonylmethylene)triphenylphosphorane. Conventional benzoylation of 4 resulted in the formation of the lactones 13a and 13b. The 3-C-(2-hydroxyethyl) analogue (5) was synthesized by lithium aluminum hydride reduction of 3,6-anhydroxy-5-azido-5-deoxy-3-C-ethoxycarbonylmethyl- 1,2-O-isopropylidene-alpha-D-glucofuranose (12), followed by deacetalation, and hydrogenation.

  DOI：

  10.1080/07328309708006509