3,6-anhydro-5-amino-5-deoxy-3-C-(2-hydroxyethyl)-1,2-O-isopropylidene-α-D-glucofuranose | 188249-23-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,6-anhydro-5-amino-5-deoxy-3-C-(2-hydroxyethyl)-1,2-O-isopropylidene-α-D-glucofuranose
• 英文别名: 2-[(1S,2R,6R,8R,9R)-9-amino-4,4-dimethyl-3,5,7,11-tetraoxatricyclo[6.3.0.02,6]undecan-1-yl]ethanol
• CAS: 188249-23-2
• 化学式: C₁₁H₁₉NO₅
• 分子量: 245.276
• InChiKey: IQYLUUCICKEYJX-DZEUPHNYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  83.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,6-anhydro-5-amino-5-deoxy-3-C-(2-hydroxyethyl)-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， 40.0 ℃ 、344.74 kPa 条件下， 反应 37.5h， 以15.3%的产率得到3,6-anhydro-1-deoxy-3-C-(2-hydroxyethyl)nojirimycin
  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 lithium aluminium tetrahydride 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 生成 3,6-anhydro-5-amino-5-deoxy-3-C-(2-hydroxyethyl)-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