(Z)-(R)-N-Boc-2,2-dimethyl-4-(4-phenyl-1-butenyl)oxazolidine | 133625-93-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (Z)-(R)-N-Boc-2,2-dimethyl-4-(4-phenyl-1-butenyl)oxazolidine
• 英文别名: tert-butyl (4R)-2,2-dimethyl-4-[(Z)-4-phenylbut-1-enyl]-1,3-oxazolidine-3-carboxylate
• CAS: 133625-93-1
• 化学式: C₂₀H₂₉NO₃
• 分子量: 331.455
• InChiKey: FPIYYSDHQPPSKF-OOXMNIKJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.55
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  38.77
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (Z)-(R)-N-Boc-2,2-dimethyl-4-(4-phenyl-1-butenyl)oxazolidine 在 Dowex 50W strong H⁺ resin 、 水 作用下， 以 甲醇 为溶剂， 以75%的产率得到(Z)-(R)-N-Boc-2-amino-6-phenyl-3-hexenol
  参考文献：
  名称：

  Synthesis of chiral vinylglycines

  摘要：

  (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.

  DOI：

  10.1021/jo00013a023
• 作为产物：
  描述：

  1-溴-3-苯基丙烷 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 2.25h， 生成 (Z)-(R)-N-Boc-2,2-dimethyl-4-(4-phenyl-1-butenyl)oxazolidine
  参考文献：
  名称：

  Synthesis of chiral vinylglycines

  摘要：

  (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.

  DOI：

  10.1021/jo00013a023

文献信息

• Alpha-galactosyl ceramide analogs and their use as immunotherapies
  申请人：Wong Chi-Huey

  公开号：US20080260774A1

  公开（公告）日：2008-10-23

  The present disclosure relates to synthetic alpha-galactosyl ceramide (α-GalCer) analogs, and their use as immunotherapies. In one aspect, a method of activating a cytokine response in a subject includes administering an effective amount of a compound to a subject, wherein the subject has an adaptive immune system that includes a population of cells, the population including at least one lymphocyte and at least one antigen-presenting cell, and wherein the compound is represented by the structure of formula 1: wherein, n is 0 to 25; X is selected from O and S; R 1 is selected from H, CH 3 , and phenyl, where phenyl is optionally substituted with H, OH, OCH 3 , F, CF 3 , phenyl, phenyl-F, C 1 -C 6 alkyl, or C 2 -C 6 branched alkyl; R 2 is selected from OH and H; R 3 is selected from C 1 -C 15 alkyl, and phenyl, where phenyl is optionally substituted with H, OH, OCH 3 , F, CF 3 , phenyl, C 1 -C 6 alkyl, or C 2 -C 6 branched alkyl; R 4 is selected from OH, OSO 3 H, OSO 3 Na, and OSO 3 K; and R 5 is selected from CH 2 OH and CO 2 H; or a pharmaceutically acceptable salt thereof; forming a complex between the compound and the antigen-presenting cell, wherein the formation of the complex results in the activation of a receptor on the lymphocyte; and activating the lymphocyte to produce the cytokine response.

  本公开涉及合成α-半乳糖基鞘氨醇（α-GalCer）类似物及其用作免疫疗法的方法。在一方面，激活受试者的细胞因子反应的方法包括向受试者施用化合物的有效量，其中，受试者具有自适应免疫系统，包括细胞群体，该群体包括至少一个淋巴细胞和至少一个抗原呈递细胞，化合物由结构式1表示：其中，n为0至25；X选自O和S；R1选自H、CH3和苯基，其中苯基可选地用H、OH、O 、F、CF3、苯基、苯基-F、C1-C6烷基或C2-C6支链烷基取代；R2选自OH和H；R3选自C1-C15烷基和苯基，其中苯基可选地用H、OH、O 、F、 、苯基、C1-C6烷基或C2-C6支链烷基取代；R4选自OH、OSO3H、OSO3Na和OSO3K；R5选自CH2OH和CO2H；或其药学上可接受的盐；在化合物和抗原呈递细胞之间形成复合物，复合物的形成导致淋巴细胞上的受体被激活；并激活淋巴细胞产生细胞因子反应。
• BEAULIEU, PIERRE L.;DUCEPPE, JEAN-SIMON;JOHNSON, CAROLYNE, J. ORG. CHEM., 56,(1991) N3, C. 4196-4204
  作者：BEAULIEU, PIERRE L.、DUCEPPE, JEAN-SIMON、JOHNSON, CAROLYNE

  DOI：——

  日期：——