(2R,3R,4S)-(4-azido-3-(benzyloxy)-5-formyl-3,4-dihydro-2H-pyran-2-yl)methyl acetate | 1171170-26-5

• 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: (2R,3R,4S)-(4-azido-3-(benzyloxy)-5-formyl-3,4-dihydro-2H-pyran-2-yl)methyl acetate
• 英文别名: [(2R,3R,4S)-4-azido-5-formyl-3-phenylmethoxy-3,4-dihydro-2H-pyran-2-yl]methyl acetate
• CAS: 1171170-26-5
• 化学式: C₁₆H₁₇N₃O₅
• 分子量: 331.328
• InChiKey: WNEHAHGDSIQADG-PMPSAXMXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  76.2
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  二碳酸二叔丁酯 、 (2R,3R,4S)-(4-azido-3-(benzyloxy)-5-formyl-3,4-dihydro-2H-pyran-2-yl)methyl acetate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 以80%的产率得到(2R,3R,4S)-(3-(benzyloxy)-4-(tert-butoxycarbonylamino)-5-formyl-3,4-dihydro-2H-pyran-2-yl)methyl acetate
  参考文献：
  名称：

  Regio- and Stereocontrolled Selective Debenzylation and Substitution Reactions of C-2 Formyl Glycals. Application in the Synthesis of Constrained β-Sugar Amino Acids

  摘要：

  O-Benzyl-protected C-2 formyl glycals are regioselectively deprotected and acetylated first at C-3 and then at C-6 upon treatment with a ZnCl2-Ac2O-AcOH reagent combination. Treatment of the thus-obtained C-3 acetate with various nucleophiles leads to substitution at C-3 with retention of stereochemistry in the galactal series, whereas mixed results were obtained with glucal-derived compounds. Two of the azido-substituted products were converted into the corresponding beta-sugar amino acids.

  DOI：

  10.1021/jo9008222
• 作为产物：
  描述：

  (2R,3R,4S)-(4-acetoxy-3-(benzyloxy)-5-formyl-3,4-dihydro-2H-pyran-2-yl)methyl acetate 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以82%的产率得到(2R,3R,4S)-(4-azido-3-(benzyloxy)-5-formyl-3,4-dihydro-2H-pyran-2-yl)methyl acetate
  参考文献：
  名称：

  Regio- and Stereocontrolled Selective Debenzylation and Substitution Reactions of C-2 Formyl Glycals. Application in the Synthesis of Constrained β-Sugar Amino Acids

  摘要：

  O-Benzyl-protected C-2 formyl glycals are regioselectively deprotected and acetylated first at C-3 and then at C-6 upon treatment with a ZnCl2-Ac2O-AcOH reagent combination. Treatment of the thus-obtained C-3 acetate with various nucleophiles leads to substitution at C-3 with retention of stereochemistry in the galactal series, whereas mixed results were obtained with glucal-derived compounds. Two of the azido-substituted products were converted into the corresponding beta-sugar amino acids.

  DOI：

  10.1021/jo9008222