methyl (4aR,6R,7R,8S,8aR)-3-((S)-3-(benzyloxy)-2-((tert-butoxycarbonyl)amino)-3-oxopropyl)-7-hydroxy-6-(hydroxymethyl)-8-((triisopropylsilyl)oxy)-4a,7,8,8a-tetrahydro-6H-pyrano[2,3-b][1,4]oxathiine-2-carboxylate | 1186468-34-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (4aR,6R,7R,8S,8aR)-3-((S)-3-(benzyloxy)-2-((tert-butoxycarbonyl)amino)-3-oxopropyl)-7-hydroxy-6-(hydroxymethyl)-8-((triisopropylsilyl)oxy)-4a,7,8,8a-tetrahydro-6H-pyrano[2,3-b][1,4]oxathiine-2-carboxylate
• CAS: 1186468-34-7
• 化学式: C₃₄H₅₃NO₁₁SSi
• 分子量: 711.946
• InChiKey: PIKOEIVNRSPVNZ-YVSKQIDISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.17
• 重原子数：
  48.0
• 可旋转键数：
  13.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  159.08
• 氢给体数：
  3.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  methyl (4aR,6R,7R,8S,8aR)-3-((S)-3-(benzyloxy)-2-((tert-butoxycarbonyl)amino)-3-oxopropyl)-7-hydroxy-6-(hydroxymethyl)-8-((triisopropylsilyl)oxy)-4a,7,8,8a-tetrahydro-6H-pyrano[2,3-b][1,4]oxathiine-2-carboxylate 在 2,2,6,6-四甲基哌啶氧化物 、 碘苯二乙酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 22.0h， 以54%的产率得到
  参考文献：
  名称：

  Cyclic glycopeptidomimetics through a versatile sugar-based scaffold

  摘要：

  Cyclic peptidomimetics are attracting structures to obtain a distinct, bioactive conformation. Even more attractive are sugar-containing cyclic peptidomimetics which present turn structures induced by the pyranose ring when incorporated in cyclic peptides. The use of a new and versatile saccharidic scaffold to achieve sugar-based peptidomimetics is here reported together with the successful synthesis of diastereomerically pure cyclic SAA peptidomimetics 15 and 16. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.04.008
• 作为产物：
  描述：

  methyl (4aR,6R,7R,8S,8aR)-3-((S)-3-(benzyloxy)-2-((tert-butoxycarbonyl)amino)-3-oxopropyl)-7-hydroxy-8-((triisopropylsilyl)oxy)-6-(((triisopropylsilyl)oxy)methyl)-4a,7,8,8a-tetrahydro-6H-pyrano[2,3-b][1,4]oxathiine-2-carboxylate 在 四丁基氟化铵 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以85%的产率得到methyl (4aR,6R,7R,8S,8aR)-3-((S)-3-(benzyloxy)-2-((tert-butoxycarbonyl)amino)-3-oxopropyl)-7-hydroxy-6-(hydroxymethyl)-8-((triisopropylsilyl)oxy)-4a,7,8,8a-tetrahydro-6H-pyrano[2,3-b][1,4]oxathiine-2-carboxylate
  参考文献：
  名称：

  Cyclic glycopeptidomimetics through a versatile sugar-based scaffold

  摘要：

  Cyclic peptidomimetics are attracting structures to obtain a distinct, bioactive conformation. Even more attractive are sugar-containing cyclic peptidomimetics which present turn structures induced by the pyranose ring when incorporated in cyclic peptides. The use of a new and versatile saccharidic scaffold to achieve sugar-based peptidomimetics is here reported together with the successful synthesis of diastereomerically pure cyclic SAA peptidomimetics 15 and 16. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.04.008