(1,8,8a-13C)-(8S,8aR)-8-hydroxy-1,5,8,8a-tetrahydrooxazolidin[3,4-a]-pyridin-3-one | 949909-96-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (1,8,8a-13C)-(8S,8aR)-8-hydroxy-1,5,8,8a-tetrahydrooxazolidin[3,4-a]-pyridin-3-one
• 英文别名: (8S,8aR)-8-hydroxy-1,5,8,8a-tetrahydro-(4,5-13C2)[1,3]oxazolo[3,4-a](2,3-13C2)pyridin-3-one
• CAS: 949909-96-0
• 化学式: C₇H₉NO₃
• 分子量: 158.12
• InChiKey: HGLFTKVZIXIWEB-CABKWTCKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1,8,8a-13C)-(8S,8aR)-8-hydroxy-1,5,8,8a-tetrahydrooxazolidin[3,4-a]-pyridin-3-one 在 四氧化锇 、 N-甲基吲哚酮 、 sodium hydride 作用下， 以 水 、 N,N-二甲基甲酰胺 、 丙酮 、 叔丁醇 为溶剂， 反应 48.5h， 生成 (1,8,8a-13C)-(6R,7R,8S,8aR)-6,7-dihydroxy-8-diphenylmethoxy-1,5,8,8a-tetrahydrooxazolidin[3,4-a]pyridin-3-one
  参考文献：
  名称：

  Synthesis and NMR experiments of (4,5,6-13C)-deoxymannojirimycin. A new entry to 13C-labeled glycosidase inhibitors

  摘要：

  The synthesis of (4,5,6-C-13)-deoxymannojirimycin is described. The route employed is based oil Sharpless asymmetric epoxidation of (1,2,3-C-13)(E)-2,4-pentadien-l-ol and uses ring-closing metathesis as a key step. The labeled compound may be easily used for protein-binding experiments using NMR spectroscopic methods. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2007.04.018
• 作为产物：
  描述：

  (1,2,3-13C)-(2S,3S)-N-allyl-2,3-epoxypentylcarbamate 在 Grubbs catalyst first generation sodium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 (1,8,8a-13C)-(8S,8aR)-8-hydroxy-1,5,8,8a-tetrahydrooxazolidin[3,4-a]-pyridin-3-one
  参考文献：
  名称：

  Synthesis and NMR experiments of (4,5,6-13C)-deoxymannojirimycin. A new entry to 13C-labeled glycosidase inhibitors

  摘要：

  The synthesis of (4,5,6-C-13)-deoxymannojirimycin is described. The route employed is based oil Sharpless asymmetric epoxidation of (1,2,3-C-13)(E)-2,4-pentadien-l-ol and uses ring-closing metathesis as a key step. The labeled compound may be easily used for protein-binding experiments using NMR spectroscopic methods. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2007.04.018

文献信息

• Synthesis and NMR experiments of (4,5,6-13C)-deoxymannojirimycin. A new entry to 13C-labeled glycosidase inhibitors
  作者：Caterina Murruzzu、Mònica Alonso、Angeles Canales、Jesus Jiménez-Barbero、Antoni Riera

  DOI：10.1016/j.carres.2007.04.018

  日期：2007.9

  The synthesis of (4,5,6-C-13)-deoxymannojirimycin is described. The route employed is based oil Sharpless asymmetric epoxidation of (1,2,3-C-13)(E)-2,4-pentadien-l-ol and uses ring-closing metathesis as a key step. The labeled compound may be easily used for protein-binding experiments using NMR spectroscopic methods. (c) 2007 Elsevier Ltd. All rights reserved.