(2S,3R,5R)-3-{(tert-butyldimethylsilyl)oxy}-2-[{(tert-butyldimethylsilyl)oxy}methyl]-5-vinylpyrrolidine | 1449498-65-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (2S,3R,5R)-3-{(tert-butyldimethylsilyl)oxy}-2-[{(tert-butyldimethylsilyl)oxy}methyl]-5-vinylpyrrolidine
• 英文别名: tert-butyl-[[(2S,3R,5R)-3-[tert-butyl(dimethyl)silyl]oxy-5-ethenylpyrrolidin-2-yl]methoxy]-dimethylsilane
• CAS: 1449498-65-0
• 化学式: C₁₉H₄₁NO₂Si₂
• 分子量: 371.711
• InChiKey: YCTWPACOGRKGIQ-YESZJQIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.32
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  30.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,3R,5R)-3-{(tert-butyldimethylsilyl)oxy}-2-[{(tert-butyldimethylsilyl)oxy}methyl]-5-vinylpyrrolidine 在 platinum(IV) oxide 、 氢气 作用下， 以 甲醇 为溶剂， 以52%的产率得到(2S,3R,5S)-3-{(tert-butyldimethylsilyl)oxy}-2-[{(tert-butyldimethylsilyl)oxy}methyl]-5-ethylpyrrolidine
  参考文献：
  名称：

  ASYMMETRIC SYNTHESIS OF 1-ALKYL-2-DEOXYIMINOFURANOSES VIA THE IRIDIUM-CATALYZED INTRAMOLECULAR CYCLIZATION OF AN ALLYLIC CARBONATE

  摘要：

  An asymmetric synthesis of 1-alkyl-2-deoxyiminofuranoses was achieved in which the Ir-catalyzed intramolecular cyclization was the key step. The diastereoselective cyclization converted an allylic carbonate into pyrrolidine derivatives. The alpha-glucosidase inhibitory activities of the prepared 2-deoxyiminofuranoses were also investigated.

  DOI：

  10.3987/com-12-s(n)99
• 作为产物：
  描述：

  (5R,6S)-6-amino-5,7-bis{(tert-butyldimethylsilyl)oxy}hept-2-en-1-yl methyl carbonate 在 bis(1,5-cyclooctadiene)diiridium(I) dichloride 、 1,5,7-三氮杂双环[4.4.0]癸-5-烯 、 (3,5-dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalen-4-yl)-bis-(1-phenyl-ethyl)-amine 作用下， 以 四氢呋喃 为溶剂， 反应 40.0h， 以62%的产率得到(2S,3R,5R)-3-{(tert-butyldimethylsilyl)oxy}-2-[{(tert-butyldimethylsilyl)oxy}methyl]-5-vinylpyrrolidine
  参考文献：
  名称：

  ASYMMETRIC SYNTHESIS OF 1-ALKYL-2-DEOXYIMINOFURANOSES VIA THE IRIDIUM-CATALYZED INTRAMOLECULAR CYCLIZATION OF AN ALLYLIC CARBONATE

  摘要：

  An asymmetric synthesis of 1-alkyl-2-deoxyiminofuranoses was achieved in which the Ir-catalyzed intramolecular cyclization was the key step. The diastereoselective cyclization converted an allylic carbonate into pyrrolidine derivatives. The alpha-glucosidase inhibitory activities of the prepared 2-deoxyiminofuranoses were also investigated.

  DOI：

  10.3987/com-12-s(n)99