N-(2-deoxy-α-D-arabinohexopyranosyl)succinimide | 168565-84-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(2-deoxy-α-D-arabinohexopyranosyl)succinimide
• 英文别名: 1-[(2S,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]pyrrolidine-2,5-dione
• CAS: 168565-84-2
• 化学式: C₁₀H₁₅NO₆
• 分子量: 245.232
• InChiKey: ZEHPXDFCPVVNJH-ZHYWTAKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  107
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(2-deoxy-α-D-arabinohexopyranosyl)succinimide 在 劳森试剂 、 吡啶 作用下， 以 四氢呋喃 、 甲苯 、 乙腈 为溶剂， 反应 10.5h， 生成 (1S,6S,7R,8S,9R)-8,9-bis-(tert-butyldimethylsiloxy)-7-(tert-butyldimethylsiloxy)methyl-6-trimethylsiloxy-11-oxa-2-azatricyclo[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
• 作为产物：
  描述：

  C₃₁H₃₃NO₆ 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 、 溶剂黄146 、 乙酸乙酯 为溶剂， 20.0 ℃ 、8.0 MPa 条件下， 反应 24.0h， 以99%的产率得到N-(2-deoxy-α-D-arabinohexopyranosyl)succinimide
  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.