3,6-dideoxy-3,6-imino-D-gluconic acid | 157598-76-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: 3,6-dideoxy-3,6-imino-D-gluconic acid
• 英文别名: (2R)-2-[(2S,3S,4R)-3,4-dihydroxypyrrolidin-2-yl]-2-hydroxyacetic acid
• CAS: 157598-76-0
• 化学式: C₆H₁₁NO₅
• 分子量: 177.157
• InChiKey: CMDOGOPKNMVQTC-KKQCNMDGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.4
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  110
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,6-dideoxy-3,6-imino-D-gluconic acid 在 盐酸 作用下， 以 水 为溶剂， 以93%的产率得到3,6-dideoxy-3,6-imino-D-glucono-1,4-lactone hydrochloride
  参考文献：
  名称：

  Deoxyiminoalditols from aldonolactones. III. Preparation of 1,4-dideoxy-1,4-imino-L-gulitol. - Evaluation of 1,4-dideoxy-1,4-iminohexitols as glycosidase inhibitors

  摘要：

  2,6-Dibromo-2,6-dideoxy-D-altrono-1,4-lactone (1) was converted into a mixture of 2,3-anhydro-6-bromo-6-deoxy-D-allono-1,4- (7) and -1.5-lactone (8), which by treatment with aqueous NH3 (25%) gave 3,6-dideoxy-3,6-imino-D-gluconic acid (9). Convertion into the 1,4-lactone 10 followed by reduction with NaBH4 gave 1,4-dideoxy-1,4-imino-L-gulitol (11). -Reduction of the dibromolactone 1 gave 2,6-dibromo-2,6-dideoxy-D-altritol (1,5-dibromo-1,5-dideoxy-D-talitol) (2) which was unstable since it was readily transformed into 3,6-anhydro-2-bromo-2-deoxy-D-altritol (3). Treatment of either 2 or 3 with aqueous NH3 (25%) gave 1-amino-1-deoxy-3,6-anhydro-D-allitol (6). -The reaction of the bromo compounds with aqueous NH3 were followed by C-13 NMR spectroscopy. -Evaluation of nine 1,4-dideoxy-1,4-iminohexitols with D- and L- allo, talo-, galacto-, ido- and with L-gulo-configurations as glycosidase inhibitors is reported.

  DOI：

  10.1016/s0040-4020(01)90479-x
• 作为产物：
  描述：

  2,6-dibromo-2,6-dideoxy-D-altrono-1,4-lactone 在 potassium fluoride 、 ammonium hydroxide 作用下， 生成 3,6-dideoxy-3,6-imino-D-gluconic acid 、 2,3-anhydro-6-bromo-6-deoxy-D-allono-1,4-lactone
  参考文献：
  名称：

  Deoxyiminoalditols from aldonolactones. III. Preparation of 1,4-dideoxy-1,4-imino-L-gulitol. - Evaluation of 1,4-dideoxy-1,4-iminohexitols as glycosidase inhibitors

  摘要：

  2,6-Dibromo-2,6-dideoxy-D-altrono-1,4-lactone (1) was converted into a mixture of 2,3-anhydro-6-bromo-6-deoxy-D-allono-1,4- (7) and -1.5-lactone (8), which by treatment with aqueous NH3 (25%) gave 3,6-dideoxy-3,6-imino-D-gluconic acid (9). Convertion into the 1,4-lactone 10 followed by reduction with NaBH4 gave 1,4-dideoxy-1,4-imino-L-gulitol (11). -Reduction of the dibromolactone 1 gave 2,6-dibromo-2,6-dideoxy-D-altritol (1,5-dibromo-1,5-dideoxy-D-talitol) (2) which was unstable since it was readily transformed into 3,6-anhydro-2-bromo-2-deoxy-D-altritol (3). Treatment of either 2 or 3 with aqueous NH3 (25%) gave 1-amino-1-deoxy-3,6-anhydro-D-allitol (6). -The reaction of the bromo compounds with aqueous NH3 were followed by C-13 NMR spectroscopy. -Evaluation of nine 1,4-dideoxy-1,4-iminohexitols with D- and L- allo, talo-, galacto-, ido- and with L-gulo-configurations as glycosidase inhibitors is reported.

  DOI：

  10.1016/s0040-4020(01)90479-x