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 | 1186468-33-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 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
• CAS: 1186468-33-6
• 化学式: C₄₃H₇₃NO₁₁SSi₂
• 分子量: 868.29
• InChiKey: AESAMQKIXDDTRF-WAYYKIQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.37
• 重原子数：
  58.0
• 可旋转键数：
  18.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  148.08
• 氢给体数：
  2.0
• 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-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
• 作为产物：
  描述：

  3,6-二-O-三异丙基硅基-D-葡萄糖醛 、 (S)-1-(2-甲氧基羰基)乙酰基-3-叔丁氧羰基氨基丙酸苄酯 在 吡啶 、 N-Chlorsulfonyl-phthalimid 作用下， 以 氯仿 为溶剂， 反应 28.0h， 以59%的产率得到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
  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