(2R,3R,4R,5R)-1,4-dideoxy-1,6-imino-3,4-O-isopropylidene-D-mannitol | 160226-26-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4R,5R)-1,4-dideoxy-1,6-imino-3,4-O-isopropylidene-D-mannitol
• 英文别名: (3aR,4R,7R,7aR)-4-(hydroxymethyl)-2,2-dimethyl-3a,4,5,6,7,7a-hexahydro-[1,3]dioxolo[4,5-c]pyridin-7-ol
• CAS: 160226-26-6
• 化学式: C₉H₁₇NO₄
• 分子量: 203.238
• InChiKey: KVGDVIZWSSLLDW-WCTZXXKLSA-N

物化性质

• 沸点：
  368.050±42.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.176±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  71
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,5R)-1,4-dideoxy-1,6-imino-3,4-O-isopropylidene-D-mannitol 在 Dowex 50W-X₈ 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以97%的产率得到1-脱氧甘露伊霉素
  参考文献：
  名称：

  Simple synthesis of (–)-deoxymannojirimycin and (2S,3R,4R,5R)-3,4,5-trihydroxypipecolic acid via regioselective hydrolysis

  摘要：

  A short and efficient synthesis of (-)-deoxymannojirimycin and (2S,3R,4R,5R)-3,4,5-trihydroxypipecolic acid is described, with D-glucono-delta-lactone as chiral educt. Key transformations included selective cleavage of a terminal isopropylidene group with Dowex 50W-X8 (H+) and intramolecular nucleophilic amination.

  DOI：

  10.1039/p19940002621
• 作为产物：
  描述：

  methyl 2-benzyloxycarbonylamino-2-deoxy-3,4-O-isopropylidene-6-O-methanesulfonyloxy-D-mannonate 在 palladium on activated charcoal lithium aluminium tetrahydride 、 氢气 、 sodium acetate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 13.0h， 生成 (2R,3R,4R,5R)-1,4-dideoxy-1,6-imino-3,4-O-isopropylidene-D-mannitol
  参考文献：
  名称：

  Simple synthesis of (–)-deoxymannojirimycin and (2S,3R,4R,5R)-3,4,5-trihydroxypipecolic acid via regioselective hydrolysis

  摘要：

  A short and efficient synthesis of (-)-deoxymannojirimycin and (2S,3R,4R,5R)-3,4,5-trihydroxypipecolic acid is described, with D-glucono-delta-lactone as chiral educt. Key transformations included selective cleavage of a terminal isopropylidene group with Dowex 50W-X8 (H+) and intramolecular nucleophilic amination.

  DOI：

  10.1039/p19940002621

文献信息

• Simple synthesis of (–)-deoxymannojirimycin and (2S,3R,4R,5R)-3,4,5-trihydroxypipecolic acid via regioselective hydrolysis
  作者：Ki Hun Park、Yong Jin Yoon、Sang Gyeong Lee

  DOI：10.1039/p19940002621

  日期：——

  A short and efficient synthesis of (-)-deoxymannojirimycin and (2S,3R,4R,5R)-3,4,5-trihydroxypipecolic acid is described, with D-glucono-delta-lactone as chiral educt. Key transformations included selective cleavage of a terminal isopropylidene group with Dowex 50W-X8 (H+) and intramolecular nucleophilic amination.