methyl (2R,3R,4S)-2-(acetyloxymethyl)-4-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylmethoxy-3,4-dihydro-2H-pyran-5-carboxylate | 1171169-83-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (2R,3R,4S)-2-(acetyloxymethyl)-4-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylmethoxy-3,4-dihydro-2H-pyran-5-carboxylate
• CAS: 1171169-83-7
• 化学式: C₂₂H₂₉NO₈
• 分子量: 435.474
• InChiKey: LBRRLVSEVHLXAE-QYZOEREBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  31
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  重氮甲烷 、 以 四氢呋喃 、 乙醚 为溶剂， 反应 0.25h， 生成 methyl (2R,3R,4S)-2-(acetyloxymethyl)-4-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylmethoxy-3,4-dihydro-2H-pyran-5-carboxylate
  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