(4R)-N-<(tert-butyloxy)carbonyl>-2,2-dimethyl-4-<(3R,1E)-4-(benzyloxy)-3-methyl-1-butenyl>oxazolidine | 127882-43-3

• 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: (4R)-N-<(tert-butyloxy)carbonyl>-2,2-dimethyl-4-<(3R,1E)-4-(benzyloxy)-3-methyl-1-butenyl>oxazolidine
• 英文别名: tert-butyl (4R)-2,2-dimethyl-4-[(E,3R)-3-methyl-4-phenylmethoxybut-1-enyl]-1,3-oxazolidine-3-carboxylate
• CAS: 127882-43-3
• 化学式: C₂₂H₃₃NO₄
• 分子量: 375.508
• InChiKey: ISZYJJYNSZUJNY-JXGFJBPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4R)-N-<(tert-butyloxy)carbonyl>-2,2-dimethyl-4-<(3R,1E)-4-(benzyloxy)-3-methyl-1-butenyl>oxazolidine 在 二异丁基氢化铝 、 臭氧 作用下， 生成 (R)-3-(benzyloxy)-2-methylpropan-1-ol
  参考文献：
  名称：

  A highly stereoselective synthesis of (E)-alkene dipeptide isosteres via organocyanocopper-Lewis acid mediation reaction

  摘要：

  A stereoselective synthesis of protected (E)-alkene dipeptide isosteres by the reaction of the mesylates of homochiral delta-aminated gamma-hydroxy (E)-alpha,beta-enoates with either RCu(CN)Li.BF3 or RCu(CN)MgX.BF3 reagent is described. The degree of diastereoselectivity has been found to be uniformly high except for the serine- and threonine-derived acetonides 77 and 81. The synthesis permits the introduction of sterically hindered appendages such as isopropyl and tert-butyl groups at the alpha position to the ester group. This methodology provides a new route to a wide range of modified (E)-alkene peptide mimics that may have biological importance.

  DOI：

  10.1021/jo00014a010
• 作为产物：
  描述：

  (R)-4-((E)-(R)-3-Methoxycarbonyl-but-1-enyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 在 sodium hydride 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 生成 (4R)-N-<(tert-butyloxy)carbonyl>-2,2-dimethyl-4-<(3R,1E)-4-(benzyloxy)-3-methyl-1-butenyl>oxazolidine
  参考文献：
  名称：

  A highly stereoselective synthesis of (E)-alkene dipeptide isosteres via organocyanocopper-Lewis acid mediation reaction

  摘要：

  A stereoselective synthesis of protected (E)-alkene dipeptide isosteres by the reaction of the mesylates of homochiral delta-aminated gamma-hydroxy (E)-alpha,beta-enoates with either RCu(CN)Li.BF3 or RCu(CN)MgX.BF3 reagent is described. The degree of diastereoselectivity has been found to be uniformly high except for the serine- and threonine-derived acetonides 77 and 81. The synthesis permits the introduction of sterically hindered appendages such as isopropyl and tert-butyl groups at the alpha position to the ester group. This methodology provides a new route to a wide range of modified (E)-alkene peptide mimics that may have biological importance.

  DOI：

  10.1021/jo00014a010

文献信息

• Ibuka, Toshiro; Habashita, Hiromu; Funakoshi, Susumu, Angewandte Chemie, 1990, vol. 102, # 7, p. 816 - 818
  作者：Ibuka, Toshiro、Habashita, Hiromu、Funakoshi, Susumu、Fujii, Nobutaka、Oguchi, Yusaku、et al.

  DOI：——

  日期：——
• IBUKA, TOSHIRO;HABASHITA, HIROMU;FUNAKOSHI, SUSUMU;FUJII, NOBUTAKA;OGUCHI+, ANGEW. CHEM., 102,(1990) N, C. 816-818
  作者：IBUKA, TOSHIRO、HABASHITA, HIROMU、FUNAKOSHI, SUSUMU、FUJII, NOBUTAKA、OGUCHI+

  DOI：——

  日期：——