(3aR,4R,7S,7aS)-7-Methoxymethoxy-2,2-dimethyl-4-trityloxymethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyridine-5-carboxylic acid tert-butyl ester | 205579-05-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (3aR,4R,7S,7aS)-7-Methoxymethoxy-2,2-dimethyl-4-trityloxymethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyridine-5-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (3aR,4R,7S,7aS)-7-(methoxymethoxy)-2,2-dimethyl-4-(trityloxymethyl)-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyridine-5-carboxylate
• CAS: 205579-05-1
• 化学式: C₃₅H₄₃NO₇
• 分子量: 589.729
• InChiKey: LMAVXBUQTUVJNV-ITGKQZKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  43
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  75.7
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (3aR,4R,7S,7aS)-7-Methoxymethoxy-2,2-dimethyl-4-trityloxymethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyridine-5-carboxylic acid tert-butyl ester 在 盐酸 、 Dowex 50W-X₈ (H⁽¹⁺⁾ form) 作用下， 生成 (2R,3R,4S,5S)-2-(hydroxymethyl)piperidine-3,4,5-triol
  参考文献：
  名称：

  Improved Synthesis of 1-Deoxynojirimycin and Facile Synthesis of Its Stereoisomers from (S)-Pyroglutamic Acid Derivative

  摘要：

  Improved synthesis of 1-deoxynojirimycin (9) from (E)-alpha,beta-unsaturated ester(1) and facile synthesis of 1-deoxyazasugars (14 and 15) from 10 where both substrates (1 and 10) prepared from (S)-pyroglutamic acid were described.

  DOI：

  10.3987/com-97-s11
• 作为产物：
  描述：

  Methanesulfonic acid (S)-2-[(4R,5R)-5-((R)-1-tert-butoxycarbonylamino-2-trityloxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-methoxymethoxy-ethyl ester 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 (3aR,4R,7S,7aS)-7-Methoxymethoxy-2,2-dimethyl-4-trityloxymethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyridine-5-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Improved Synthesis of 1-Deoxynojirimycin and Facile Synthesis of Its Stereoisomers from (S)-Pyroglutamic Acid Derivative

  摘要：

  Improved synthesis of 1-deoxynojirimycin (9) from (E)-alpha,beta-unsaturated ester(1) and facile synthesis of 1-deoxyazasugars (14 and 15) from 10 where both substrates (1 and 10) prepared from (S)-pyroglutamic acid were described.

  DOI：

  10.3987/com-97-s11