(3R,4R)-3-(N-benzylhydroxyamino)-4-(tert-butoxycarbonylamino)-5-(tert-butyldiphenylsiloxy)-1-pentene | 299409-55-5

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (3R,4R)-3-(N-benzylhydroxyamino)-4-(tert-butoxycarbonylamino)-5-(tert-butyldiphenylsiloxy)-1-pentene
• 英文别名: tert-butyl N-[(2R,3R)-3-[benzyl(hydroxy)amino]-1-[tert-butyl(diphenyl)silyl]oxypent-4-en-2-yl]carbamate
• CAS: 299409-55-5
• 化学式: C₃₃H₄₄N₂O₄Si
• 分子量: 560.809
• InChiKey: DJAUUBVGGKREFB-XZWHSSHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  40
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  71
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3R,4R)-3-(N-benzylhydroxyamino)-4-(tert-butoxycarbonylamino)-5-(tert-butyldiphenylsiloxy)-1-pentene 在 copper diacetate 、 锌 作用下， 以 溶剂黄146 为溶剂， 反应 1.0h， 以72%的产率得到(3R,4R)-3-benzylamino-4-(tert-butoxycarbonylamino)-5-(tert-butyldiphenylsiloxy)-1-pentene
  参考文献：
  名称：

  A General Method for the Vinylation of Nitrones. Synthesis of Allyl Hydroxylamines and Allyl Amines

  摘要：

  An examination of the vinylation of several nitrones is presented. Whereas a complete diastereofacial discrimination was observed upon the addition of vinyl organometallic reagents to alpha-alkoxy nitrones, the same reaction with alpha-amino nitrones pave syn adducts in all cases, with the only exception of a L-serine-derived alpha-amino monoprotected nitrone. The obtained allyl hydroxylamines were easily transformed into synthetically valuable allyl amines.

  DOI：

  10.1080/00397910008087449
• 作为产物：
  描述：

  乙烯基溴化镁 、 (Z)-N-[(2R)-2-(tert-butoxycarbonylamino)-3-(tertbutyldiphenylsilyloxy)-propylidene]benzylamine N-oxide 以 四氢呋喃 为溶剂， 反应 2.0h， 以77%的产率得到(3R,4R)-3-(N-benzylhydroxyamino)-4-(tert-butoxycarbonylamino)-5-(tert-butyldiphenylsiloxy)-1-pentene
  参考文献：
  名称：

  A General Method for the Vinylation of Nitrones. Synthesis of Allyl Hydroxylamines and Allyl Amines

  摘要：

  An examination of the vinylation of several nitrones is presented. Whereas a complete diastereofacial discrimination was observed upon the addition of vinyl organometallic reagents to alpha-alkoxy nitrones, the same reaction with alpha-amino nitrones pave syn adducts in all cases, with the only exception of a L-serine-derived alpha-amino monoprotected nitrone. The obtained allyl hydroxylamines were easily transformed into synthetically valuable allyl amines.

  DOI：

  10.1080/00397910008087449

文献信息

• A General Method for the Vinylation of Nitrones. Synthesis of Allyl Hydroxylamines and Allyl Amines
  作者：Pedro Merino、Sonia Anoro、Santiago Franco、Jose M. Gascon、Victor Martin、Francisco L. Merchan、Julia Revuelta、Tomas Tejero、Victoria Tuñon

  DOI：10.1080/00397910008087449

  日期：2000.8

  An examination of the vinylation of several nitrones is presented. Whereas a complete diastereofacial discrimination was observed upon the addition of vinyl organometallic reagents to alpha-alkoxy nitrones, the same reaction with alpha-amino nitrones pave syn adducts in all cases, with the only exception of a L-serine-derived alpha-amino monoprotected nitrone. The obtained allyl hydroxylamines were easily transformed into synthetically valuable allyl amines.