(2R,3R,4R)-3-amino-N-<(tert-butyloxy)carbonyl>-2,4-dihydroxy-2,3-O,N-isopropylidene-5-hexene | 134210-37-0

• 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: (2R,3R,4R)-3-amino-N-<(tert-butyloxy)carbonyl>-2,4-dihydroxy-2,3-O,N-isopropylidene-5-hexene
• 英文别名: tert-butyl (4R,5R)-4-[(1R)-1-hydroxyprop-2-enyl]-2,2,5-trimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 134210-37-0
• 化学式: C₁₄H₂₅NO₄
• 分子量: 271.357
• InChiKey: ICZYTPFXNJYAKX-MXWKQRLJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.29
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  59.0
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R)-3-amino-N-<(tert-butyloxy)carbonyl>-2,4-dihydroxy-2,3-O,N-isopropylidene-5-hexene 在 吡啶 、 4-二甲氨基吡啶 、 lithium chloride 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 21.0h， 生成 (4E,2R,3R)-3-amino-N-<(tert-butyloxy)carbonyl>-2-hydroxy-2,3-O,N-isopropylidene-4,7-octadiene
  参考文献：
  名称：

  Remarkable difference in reactivity of ordinary vinylcopper reagents and vinylzinc halide containing a copper salt towards γ-mesyloxy-α, β-enoates. Synthesis of homochiral 1,4-dienes

  摘要：

  Whereas the reaction of gamma-mesyloxy alpha,beta-enoates with vinyl-Cu(CN)M or (vinyl)2Cu(CN)M2 (M = Li or MgX) yielded a reduction product with an (E)-double bond at the beta,gamma-position, treatment of the same substrates with ''higher order'' zinc cuprate reagents or vinyl-ZnCl by the addition of catalytic amount of Cu(I) or Cu(II) salt afforded alpha- and gamma-vinylation products. Both vinylation products were stable 1,4-diene derivatives that are only more difficulty accessed by more traditional means.

  DOI：

  10.1016/s0040-4020(01)80217-9
• 作为产物：
  描述：

  (2R,4R,3S)-3-amino-N-<(tert-butyloxy)carbonyl>-2,4-dihydroxy-5-hexene 、 2,2-二甲氧基丙烷 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以87%的产率得到(2R,3R,4R)-3-amino-N-<(tert-butyloxy)carbonyl>-2,4-dihydroxy-2,3-O,N-isopropylidene-5-hexene
  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