(3S,4R,6S)-2,3,4-triacetoxy-1-aza-8-oxabicyclo[4.3.0]nonan-9-one | 1010732-16-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环庚烷
• 英文名称: (3S,4R,6S)-2,3,4-triacetoxy-1-aza-8-oxabicyclo[4.3.0]nonan-9-one
• 英文别名: [(6S,7R,8aS)-5,6-diacetyloxy-3-oxo-1,5,6,7,8,8a-hexahydro-[1,3]oxazolo[3,4-a]pyridin-7-yl] acetate
• CAS: 1010732-16-7
• 化学式: C₁₃H₁₇NO₈
• 分子量: 315.28
• InChiKey: LMDCHOQVRWWIGH-PSIUFMSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  108
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (3S,4R,6S)-2,3,4-triacetoxy-1-aza-8-oxabicyclo[4.3.0]nonan-9-one 在 三乙基硅烷 、 甲烷磺酸 作用下， 生成 (3R,4R,6S)-3,4-diacetoxy-1-aza-8-oxabicyclo[4.3.0]nonan-9-one
  参考文献：
  名称：

  Stereoselective synthesis of azasugars by electrochemical oxidation

  摘要：

  A new method using electrochemical oxidation has been exploited for the stereoselective synthesis of 2,3,6-trihydroxylated 5S-piperidine derivatives. The electrochemical method was Successively used for the conversion of N-protected piperidines to N-protected 1-methoxypiperidines and for the conversion of 1-methoxy-2,3-didehydropiperidine derivatives to 1,2,3-triacetoxypiperidine derivatives. The method provided a new synthetic route to 2S,3S,6-triacetoxy-5S-methylpiperidine and 2R,3R,6-triacetoxy-5S-methylpiperidine. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.09.036
• 作为产物：
  描述：

  (S,S)-piperidinedicarboxylic acid dimethyl ester 在 sodium tetrahydroborate 、 溴 、 sodium methylate 、 potassium acetate 作用下， 以 甲醇 、 乙二醇二甲醚 为溶剂， 生成 (3S,4R,6S)-2,3,4-triacetoxy-1-aza-8-oxabicyclo[4.3.0]nonan-9-one
  参考文献：
  名称：

  Stereoselective synthesis of azasugars by electrochemical oxidation

  摘要：

  A new method using electrochemical oxidation has been exploited for the stereoselective synthesis of 2,3,6-trihydroxylated 5S-piperidine derivatives. The electrochemical method was Successively used for the conversion of N-protected piperidines to N-protected 1-methoxypiperidines and for the conversion of 1-methoxy-2,3-didehydropiperidine derivatives to 1,2,3-triacetoxypiperidine derivatives. The method provided a new synthetic route to 2S,3S,6-triacetoxy-5S-methylpiperidine and 2R,3R,6-triacetoxy-5S-methylpiperidine. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.09.036

文献信息

• Stereoselective synthesis of 3-deoxy-piperidine iminosugars from l-lysine
  作者：Noriaki Moriyama、Yoshihiro Matsumura、Masami Kuriyama、Osamu Onomura

  DOI：10.1016/j.tetasy.2009.11.028

  日期：2009.12

  A new method using electrochemical oxidation and/or OsO4 oxidation has been used for the stereoselective synthesis of 2,3,6-trihydroxylated (5S)-piperidine derivatives. The electrochemical method was successively used for the conversion of N-protected piperidines to N-protected 1-methoxpiperidines and for the conversion of 2,3-didehydro-1-methoxypiperidine derivatives to 2,3-trans-1,2,3-triacetoxypiperidine derivatives. These triacetates were easily transformed into (2S,3S)-6-triacetoxy-(5S)-methylpiperidine and (2R,3R)-6-triacetoxy-(5S)-methylpiperidine. In addition, the 2,3-cis-dihydroxylation of 2,3-didehydro-1-methoxypiperidine derivatives with OsO4 afforded (2R,3S)-6-triacetoxy-(5S)-methylpiperidine and (2S,3R)-(3-triacetoxy-(5S)-methylpiperidine. (C) 2009 Elsevier Ltd. All rights reserved.