(2S,3R,4R,5R)-methyl 2,6-dideoxy-2,6-imino-3,4-O-isopropylidene-D-mannonate | 160147-90-0

• 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: (2S,3R,4R,5R)-methyl 2,6-dideoxy-2,6-imino-3,4-O-isopropylidene-D-mannonate
• 英文别名: methyl (3aR,4S,7R,7aR)-7-hydroxy-2,2-dimethyl-3a,4,5,6,7,7a-hexahydro-[1,3]dioxolo[4,5-c]pyridine-4-carboxylate
• CAS: 160147-90-0
• 化学式: C₁₀H₁₇NO₅
• 分子量: 231.249
• InChiKey: ZOKUPLMBDJUGSI-ULAWRXDQSA-N

物化性质

• 沸点：
  350.818±42.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.206±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  77
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,3R,4R,5R)-methyl 2,6-dideoxy-2,6-imino-3,4-O-isopropylidene-D-mannonate 在 lithium aluminium tetrahydride 、 Dowex 50W-X₈ 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 6.0h， 生成 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-azido-2-deoxy-3,4:5,6-di-O-isopropylidene-D-mannonate 在 palladium on activated charcoal Dowex 50W-X₈ resin 、 水 、 氢气 、 sodium acetate 、 sodium carbonate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 32.67h， 生成 (2S,3R,4R,5R)-methyl 2,6-dideoxy-2,6-imino-3,4-O-isopropylidene-D-mannonate
  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.