(2S,5R)-2-((4R,5R)-5-Azidomethyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-5-isopropyl-3,6-dimethoxy-2,5-dihydro-pyrazine | 159610-85-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,5R)-2-((4R,5R)-5-Azidomethyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-5-isopropyl-3,6-dimethoxy-2,5-dihydro-pyrazine
• CAS: 159610-85-2
• 化学式: C₁₆H₂₇N₅O₄
• 分子量: 353.421
• InChiKey: YKOKUZSIQBNCPG-UMSGYPCISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  110.4
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (2S,5R)-2-((4R,5R)-5-Azidomethyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-5-isopropyl-3,6-dimethoxy-2,5-dihydro-pyrazine 在 palladium on activated charcoal 盐酸 、 lithium hydroxide 、 氢气 、 碳酸氢钠 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 26.0h， 生成 (S)-2-Amino-3-[(4R,5R)-5-({[(4R,5R)-5-((S)-2-amino-2-carboxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl]-benzyloxycarbonyl-amino}-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-propionic acid
  参考文献：
  名称：

  Synthesis of orthogonally protected hydroxylated azalkene-α,α′-bridged bis(α-glycine) and dihydroxylysine derivatives

  摘要：

  Stereoselective syntheses of hydroxylated azalkene-alpha,alpha'-bridged bis(alpha-glycine) derivatives and lysine derivatives are described. The bridge was formed as a secondary amine by a reductive dimerization process of two azide molecules upon hydrogenolysis over 5% palladium-on-charcoal. Lysine derivatives were formed by reduction of the azide function to a primary amine. In the target amino acids the vicinal dihydroxy functions were protected as acetonides, the N'-amino group as a Z-derivative and the alpha-amino groups as Fmoc-derivatives. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00094-9
• 作为产物：
  描述：

  (2S,5R)-2-((4R,5S)-5-Bromomethyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-5-isopropyl-3,6-dimethoxy-2,5-dihydro-pyrazine 在 sodium azide 、 四丁基碘化铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 以82%的产率得到(2S,5R)-2-((4R,5R)-5-Azidomethyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-5-isopropyl-3,6-dimethoxy-2,5-dihydro-pyrazine
  参考文献：
  名称：

  Synthesis of orthogonally protected hydroxylated azalkene-α,α′-bridged bis(α-glycine) and dihydroxylysine derivatives

  摘要：

  Stereoselective syntheses of hydroxylated azalkene-alpha,alpha'-bridged bis(alpha-glycine) derivatives and lysine derivatives are described. The bridge was formed as a secondary amine by a reductive dimerization process of two azide molecules upon hydrogenolysis over 5% palladium-on-charcoal. Lysine derivatives were formed by reduction of the azide function to a primary amine. In the target amino acids the vicinal dihydroxy functions were protected as acetonides, the N'-amino group as a Z-derivative and the alpha-amino groups as Fmoc-derivatives. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00094-9