(3aS,6S,7R,7aS)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-7-hydroxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyridin-4-one | 214897-79-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (3aS,6S,7R,7aS)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-7-hydroxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyridin-4-one
• CAS: 214897-79-7
• 化学式: C₁₅H₂₉NO₅Si
• 分子量: 331.484
• InChiKey: JKIJSGZGPWTVJE-USZNOCQGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.39
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  77.02
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (3aS,6S,7R,7aS)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-7-hydroxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyridin-4-one 在 三氟乙酸 作用下， 反应 4.0h， 以90%的产率得到(3S,4S,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)piperidin-2-one
  参考文献：
  名称：

  5-epi-Deoxyrhamnojirimycin is a potent inhibitor of an α-l-rhamnosidase: 5-epi-deoxymannojirimycin is not a potent inhibitor of an α-d-mannosidase

  摘要：

  Whereas deoxyrhamnojirimycin (LRJ) 1 shows no significant inhibition of naringinase (an alpha-L-rhamnosidase), its C-5 epimer 2 is a potent and specific inhibitor of the enzyme and demonstrates the value of unambiguous chemical synthesis of such materials in the evaluation of their biological properties. In contrast, moderately weak inhibition towards an alpha-D-mannosidase is shown by both deoxymannojirimycin (DMJ) 5 and its C-5 epimer 6. Mimics of L-rhamnose which are recognised by enzymes that synthesise or process L-rhamnose may inhibit el ther the biosynthesis of the sugar or its incorporation into mycobacterial cell walls, providing new strategies for the treatment of diseases such as tuberculosis and leprosy. Molecular modelling studies provide a rationale for the surprisingly potent activity of the C-S epimer 2 compared with LRJ 1 and support a general hypothesis that potent piperidine glycosidase inhibitors mimic the H-4(3) conformation Of the relevant glycopyranosyl cation intermediate. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00317-6
• 作为产物：
  描述：

  5-Azido-6-(tert-butyldimethylsilyl)-2,3-O-isopropylidene L-Gulono-1,4-lactone 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 23.0h， 以80%的产率得到(3aS,6S,7R,7aS)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-7-hydroxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyridin-4-one
  参考文献：
  名称：

  5-epi-Deoxyrhamnojirimycin is a potent inhibitor of an α-l-rhamnosidase: 5-epi-deoxymannojirimycin is not a potent inhibitor of an α-d-mannosidase

  摘要：

  Whereas deoxyrhamnojirimycin (LRJ) 1 shows no significant inhibition of naringinase (an alpha-L-rhamnosidase), its C-5 epimer 2 is a potent and specific inhibitor of the enzyme and demonstrates the value of unambiguous chemical synthesis of such materials in the evaluation of their biological properties. In contrast, moderately weak inhibition towards an alpha-D-mannosidase is shown by both deoxymannojirimycin (DMJ) 5 and its C-5 epimer 6. Mimics of L-rhamnose which are recognised by enzymes that synthesise or process L-rhamnose may inhibit el ther the biosynthesis of the sugar or its incorporation into mycobacterial cell walls, providing new strategies for the treatment of diseases such as tuberculosis and leprosy. Molecular modelling studies provide a rationale for the surprisingly potent activity of the C-S epimer 2 compared with LRJ 1 and support a general hypothesis that potent piperidine glycosidase inhibitors mimic the H-4(3) conformation Of the relevant glycopyranosyl cation intermediate. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00317-6