(Z,R)-3-t-butoxycarbonyl-2,2-dimethyl-4-(1-propenyl)-1,3-oxazolidine | 133625-90-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (Z,R)-3-t-butoxycarbonyl-2,2-dimethyl-4-(1-propenyl)-1,3-oxazolidine
• 英文别名: (Z)-(R)-N-Boc-2,2-dimethyl-4-(1-propenyl)oxazolidine；tert-butyl (4R)-2,2-dimethyl-4-[(Z)-prop-1-enyl]-1,3-oxazolidine-3-carboxylate
• CAS: 133625-90-8
• 化学式: C₁₃H₂₃NO₃
• 分子量: 241.331
• InChiKey: HPCPFFAFEZSLCK-GQYWMQPJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z,R)-3-t-butoxycarbonyl-2,2-dimethyl-4-(1-propenyl)-1,3-oxazolidine 在 对甲苯磺酸 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 50.0h， 生成 (2S,3R,4R)-2-tert-butoxycarbonylamino-4-methoxypentane-1,3-diol
  参考文献：
  名称：

  由N-烷氧基羰基氨基环氧化物合成手性恶唑烷-2-酮的计算研究

  摘要：

  苏- ñ -Alkoxycarbonylamino环氧化物 5a–d，包含恶唑烷通过氨基甲酸酯部分对质子化的环氧乙烷环的亲核分子内攻击，通过总的区域和立体选择将其转化为反式-4,5-二取代的2-恶唑烷丁-2-酮2。理论计算证实了环氨基甲酸酯化反应的区域选择和偏好与分子间攻击的选择性。溶剂与类似的碘鎓离子相比，是由不同的行为引起的。

  DOI：

  10.1039/b203702e
• 作为产物：
  描述：

  3-反-溴碳-2,2'-二甲基氧酸酯 生成 (Z,R)-3-t-butoxycarbonyl-2,2-dimethyl-4-(1-propenyl)-1,3-oxazolidine
  参考文献：
  名称：

  BEAULIEU, PIERRE L.;DUCEPPE, JEAN-SIMON;JOHNSON, CAROLYNE, J. ORG. CHEM., 56,(1991) N3, C. 4196-4204

  摘要：

  DOI：

文献信息

• Highly regio- and stereoselective iodocyclization of chiral 3-alkoxycarbonyl-4-propenyl-2,2-dimethyl-1,3-oxazolidines: a computational investigation
  作者：Juan Miquel Jordá-Gregori、M.Eugenia González-Rosende、José Sepúlveda-Arques、Roberta Galeazzi、Mario Orena

  DOI：10.1016/s0957-4166(99)00084-1

  日期：1999.3

  The iodocyclization of allylic carbamates 3a and 3b proceeded with high regio- and stereoselection to give 2-oxobicyclo[4.3.0]nonane 5a as the major product. Both the regio- and diastereoselection of the reaction were investigated with the help of molecular mechanics and quantomechanical calculations. The energetic difference between the competing transition states TS-5a and TS-5b is in good agreement

  烯丙基氨基甲酸酯3a和3b的碘环化进行高区域和立体选择，得到2-氧代双环[4.3.0]壬烷5a作为主要产物。借助分子力学和量子力学计算研究了反应的区域和非对映异构。竞争过渡态TS- 5a和TS- 5b之间的能量差异与实验结果高度吻合，从计算的过渡结构来看，空间因素似乎指导区分。
• Carbohydrate-glycolipid conjugate vaccines
  申请人：Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V.

  公开号：US10588962B2

  公开（公告）日：2020-03-17

  The present invention relates to the field of synthesizing and biologically evaluating of a novel class of carbohydrate-based vaccines. The new vaccines consist of a multi-modular structure which allows applying the vaccine to a whole variety of pathogenes. This method allows preparing vaccines against all pathogens expressing immunogenic carbohydrate antigens. As conjugation of antigenic carbohydrates to proteins is not required the conjugate vaccine is particularly heat stable. No refrigeration is required, a major drawback of protein-based vaccines.

  本发明涉及一类基于碳水化合物的新型疫苗的合成和生物评估领域。这种新型疫苗由多模块结构组成，可将疫苗应用于各种病原体。这种方法可以制备出针对所有表达免疫原性碳水化合物抗原的病原体的疫苗。由于不需要将抗原碳水化合物与蛋白质共轭，共轭疫苗的热稳定性特别好。无需冷藏，这是基于蛋白质的疫苗的一个主要缺点。
• Synthesis of chiral vinylglycines
  作者：Pierre L. Beaulieu、Jean Simon Duceppe、Carolyne Johnson

  DOI：10.1021/jo00013a023

  日期：1991.6

  (R)- or (S)-benzyl 4-formyl-2,2-dimethyl-3-oxazolidinecarboxylate (7a) and (R)- or (S)-1,1-dimethylethyl 4-formyl-2,2-dimethyl-3-oxazolidinecarboxylate (7b), readily available from serine, react with Wittig reagents to give alkenes 8. Selective deprotection followed by oxidation of the resulting unsaturated amino alcohols 9 provides vinylglycines 5 of defined configuration (> 95% ee) and double-bond geometry. D-Vinylglycines are obtained from L-serine, and conversely, D-serine gives beta,gamma-unsaturated amino acids with the L configuration. The double-bond geometry is controlled by the nature of the phosphorous ylide employed. The scope and limitations of this new methodology for the preparation of chiral vinylglycines is examined.
• Glycolipids And Analogues Thereof As Antigens For NKT Cells
  申请人：Tsuji Moriya

  公开号：US20070238871A1

  公开（公告）日：2007-10-11

  This invention relates to immunogenic compounds which serve as ligands for NKT (natural killer T) cells and to methods of use thereof in modulating immune responses.
• GLYCOLIPIDS AND ANALOGUES THEREOF AS ANTIGENS FOR NK T CELLS
  申请人：Steinman Ralph M.

  公开号：US20090117089A1

  公开（公告）日：2009-05-07

  This invention relates to immunogenic compounds which may serve as ligands for NKT (natural killer T) cells and to methods of use thereof in modulating immune responses.