tert-butyl (2R,3S,4S)-3-(benzyloxy)-2-(benzyloxymethyl)-5-formyl-3,4-dihydro-2H-pyran-4-ylcarbamate | 1171170-47-0

• 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: tert-butyl (2R,3S,4S)-3-(benzyloxy)-2-(benzyloxymethyl)-5-formyl-3,4-dihydro-2H-pyran-4-ylcarbamate
• 英文别名: tert-butyl N-[(2R,3S,4S)-5-formyl-3-phenylmethoxy-2-(phenylmethoxymethyl)-3,4-dihydro-2H-pyran-4-yl]carbamate
• CAS: 1171170-47-0
• 化学式: C₂₆H₃₁NO₆
• 分子量: 453.535
• InChiKey: ATZCOLJXNLNTBS-TZRRMPRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  33
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl (2R,3S,4S)-3-(benzyloxy)-2-(benzyloxymethyl)-5-formyl-3,4-dihydro-2H-pyran-4-ylcarbamate 在 sodium chlorite 、 sodium dihydrogenphosphate 、 水 、 间苯二酚 、 溶剂黄146 作用下， 以 叔丁醇 、 水 为溶剂， 生成
  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：

  二碳酸二叔丁酯 、 (2R,3S,4S)-4-azido-3-(benzyloxy)-2-(benzyloxymethyl)-3,4-dihydro-2H-pyran-5-carbaldehyde 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 以78%的产率得到tert-butyl (2R,3S,4S)-3-(benzyloxy)-2-(benzyloxymethyl)-5-formyl-3,4-dihydro-2H-pyran-4-ylcarbamate
  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

文献信息

• Regio- and Stereocontrolled Selective Debenzylation and Substitution Reactions of C<i>-</i>2 Formyl Glycals. Application in the Synthesis of Constrained β-Sugar Amino Acids
  作者：Girish K. Rawal、Shikha Rani、Nitee Kumari、Yashwant D. Vankar

  DOI：10.1021/jo9008222

  日期：2009.8.7

  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.