N-(3,4,6-tri-O-tert-butyldimethylsilyl-2-deoxy-α-D-arabinohexopyranosyl)succinimide

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(3,4,6-tri-O-tert-butyldimethylsilyl-2-deoxy-α-D-arabinohexopyranosyl)succinimide
• 英文别名: TBDMS(-3)[TBDMS(-4)][TBDMS(-6)]2-deoxy-D-araHex(a)-Su；1-[(2S,4R,5R,6R)-4,5-bis[[tert-butyl(dimethyl)silyl]oxy]-6-[[tert-butyl(dimethyl)silyl]oxymethyl]oxan-2-yl]pyrrolidine-2,5-dione
• 化学式: C₂₈H₅₇NO₆Si₃
• 分子量: 588.02
• InChiKey: DXOJKISMFODKDF-ZLSIYFNSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.05
• 重原子数：
  38
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  74.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(3,4,6-tri-O-tert-butyldimethylsilyl-2-deoxy-α-D-arabinohexopyranosyl)succinimide 在 劳森试剂 、 吡啶 作用下， 以 四氢呋喃 、 乙醇 、 水 、 甲苯 、 乙腈 为溶剂， 反应 5.55h， 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)]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：

  1-((2S,3S,4S,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-3-iodotetrahydro-2H-pyran-2-yl)pyrrolidine-2,5-dione 在 吡啶 、 palladium 10% on activated carbon 、 氢气 、 三正丁基氢锡 作用下， 以 四氢呋喃 、 甲醇 、 溶剂黄146 、 乙酸乙酯 为溶剂， -80.0~20.0 ℃ 、8.0 MPa 条件下， 反应 29.0h， 生成 N-(3,4,6-tri-O-tert-butyldimethylsilyl-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

• Syntheses of sugar-derived heterotricyclic lactams
  作者：Carsten E. Sowa、J�rgen Kopf、Joachim Thiem

  DOI：10.1039/c39950000211

  日期：——

  Following stereoselective addition of N-iodosuccinimide towards glycals and subsequent dehalogenation, glycosylimides 1 and 2 are obtained and converted by irradiation to yield the azepindione derivatives 3 and 4 and the [5.3.1.02,6] tricyclic alcohols 5 and 6; their prolonged irradiation gives highly functionalised bridged heterotricyclic lactams 10 and 11 with a cyclopentane backbone.

  在糖醛上通过立体选择性加成N-碘代丁二酰亚胺并随后脱卤后，得到糖基亚胺1和2，并通过辐射转化得到氮杂环丁二酮衍生物3和4以及[5.3.1.02,6]三环醇5和6；延长辐射时间可得到具有高度官能化的桥式杂三环内酰胺10和11，其骨架为环戊烷。
• Sowa, Carsten Endres; Thiem, Joachim, Angewandte Chemie, 1994, vol. 106, # 19, p. 2041 - 2043
  作者：Sowa, Carsten Endres、Thiem, Joachim

  DOI：——

  日期：——
• 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.