(1S,6S,7R,8S,9R)-8,9-dimethoxy-7-methoxymethyl-6-trimethylsiloxy-11-oxa-2-aza-tricyclo[5.3.1.0(2,6)]undecan-3-thione | 1316849-05-4

• 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: (1S,6S,7R,8S,9R)-8,9-dimethoxy-7-methoxymethyl-6-trimethylsiloxy-11-oxa-2-aza-tricyclo[5.3.1.0(2,6)]undecan-3-thione
• 英文别名: (1S,6S,7R,8S,9R)-8,9-dimethoxy-7-(methoxymethyl)-6-trimethylsilyloxy-11-oxa-2-azatricyclo[5.3.1.02,6]undecane-3-thione
• CAS: 1316849-05-4
• 化学式: C₁₆H₂₉NO₅SSi
• 分子量: 375.561
• InChiKey: GWOXLONTKQJZJV-IVCRCZCHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.13
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  81.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1S,6S,7R,8S,9R)-8,9-dimethoxy-7-methoxymethyl-6-trimethylsiloxy-11-oxa-2-aza-tricyclo[5.3.1.0(2,6)]undecan-3-thione 在 Raney nickel 作用下， 以 乙醇 、 水 为溶剂， 反应 0.05h， 以51%的产率得到(1S,6S,7R,8S,9R)-8,9-dimethoxy-7-methoxymethyl-6-trimethylsiloxy-11-oxa-2-aza-tricyclo[5.3.1.0(2,6)]undecane
  参考文献：
  名称：

  En route to sugar–alkaloid conjugates

  摘要：

  After stereoselective addition of N-iodosuccinimide to glycals subsequent dehalogenation results in formation of N-glycopyranosyl succinimides. By UV irradiation both azepindiones and preferentially [5.3.1.0(2,6)] tricyclic oxalactams could be obtained. Their transformation into a number of novel sugar conjugates resembling some prominent alkaloid N-pyrrol components by thiation and reduction is reported. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.04.022
• 作为产物：
  描述：

  3,4,6-三-O-甲基-D-葡萄糖醛 在 劳森试剂 、 吡啶 、 4-二甲氨基吡啶 、 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 33.0h， 生成 (1S,6S,7R,8S,9R)-8,9-dimethoxy-7-methoxymethyl-6-trimethylsiloxy-11-oxa-2-aza-tricyclo[5.3.1.0(2,6)]undecan-3-thione
  参考文献：
  名称：

  En route to sugar–alkaloid conjugates

  摘要：

  After stereoselective addition of N-iodosuccinimide to glycals subsequent dehalogenation results in formation of N-glycopyranosyl succinimides. By UV irradiation both azepindiones and preferentially [5.3.1.0(2,6)] tricyclic oxalactams could be obtained. Their transformation into a number of novel sugar conjugates resembling some prominent alkaloid N-pyrrol components by thiation and reduction is reported. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.04.022

文献信息

• En route to sugar–alkaloid conjugates
  作者：Carsten-Endres Sowa、Joachim Thiem

  DOI：10.1016/j.carres.2011.04.022

  日期：2011.9

  After stereoselective addition of N-iodosuccinimide to glycals subsequent dehalogenation results in formation of N-glycopyranosyl succinimides. By UV irradiation both azepindiones and preferentially [5.3.1.0(2,6)] tricyclic oxalactams could be obtained. Their transformation into a number of novel sugar conjugates resembling some prominent alkaloid N-pyrrol components by thiation and reduction is reported. (C) 2011 Elsevier Ltd. All rights reserved.