methyl 2-benzyloxycarbonylamino-2-deoxy-3,4-O-isopropylidene-D-mannonate | 160147-88-6

• 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: methyl 2-benzyloxycarbonylamino-2-deoxy-3,4-O-isopropylidene-D-mannonate
• 英文别名: methyl (2S)-2-[(4R,5R)-5-[(1R)-1,2-dihydroxyethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-2-(phenylmethoxycarbonylamino)acetate
• CAS: 160147-88-6
• 化学式: C₁₈H₂₅NO₈
• 分子量: 383.398
• InChiKey: DMAIYUPYXUXYPE-LXTVHRRPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  124
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 2-benzyloxycarbonylamino-2-deoxy-3,4-O-isopropylidene-D-mannonate 在 palladium on activated charcoal lithium aluminium tetrahydride 、 Dowex 50W-X₈ 、 氢气 、 sodium acetate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 16.17h， 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 carbonate 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 22.5h， 生成 methyl 2-benzyloxycarbonylamino-2-deoxy-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

• Efficient cleavage of terminal acetonide group: Chirospecific synthesis of 2,5-dideoxy-2,5-imino-D-mannitol
  作者：Ki Hun Park、Yong Jin Yoon、Sang Gyeong Lee

  DOI：10.1016/0040-4039(94)88373-4

  日期：1994.12

  Dowex 50W-X8 was efficient catalyst for selective cleavage of terminal actonide including acid-sensitive multifunctional groups. A facile and economically synthesis of DMDP (2,5-dideoxy-2,5-imino-D-mannitol) is described via selective hydrolysis and intramolecular nucleophilic amination.

  Dowex 50W-X8是选择性裂解包括酸敏感多官能团的末端terminal化物的有效催化剂。通过选择性水解和分子内亲核胺化反应，可以轻松，经济地合成DMDP（2,5-dideoxy-2,5-imino-D-甘露醇）。
• 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.