Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-[(2R,6S)-4-(tert-butyl-dimethyl-silanyloxy)-6-(4-nitro-phenyl)-5,6-dihydro-2H-pyran-2-yloxy]-tetrahydro-pyran-4-yl ester | 162299-79-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-[(2R,6S)-4-(tert-butyl-dimethyl-silanyloxy)-6-(4-nitro-phenyl)-5,6-dihydro-2H-pyran-2-yloxy]-tetrahydro-pyran-4-yl ester
• CAS: 162299-79-8
• 化学式: C₃₁H₄₃NO₁₄Si
• 分子量: 681.766
• InChiKey: UVSSLJSITVQSNA-KYVQYRAFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.39
• 重原子数：
  47.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  185.26
• 氢给体数：
  0.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-[(2R,6S)-4-(tert-butyl-dimethyl-silanyloxy)-6-(4-nitro-phenyl)-5,6-dihydro-2H-pyran-2-yloxy]-tetrahydro-pyran-4-yl ester 在 三氟乙酸 作用下， 以87%的产率得到(S)-2-(4-nitrophenyl)-2,3-dihydro-4H-pyran-4-one
  参考文献：
  名称：

  Hetero Diels-Alder reaction involving (E)-3-(tert-butyldimethylsiloxy)-1-(2′,3′,4′,6′-tetra- O-acetyl-β-d-glucopyranosyloxy)buta-1,3-diene and p-nitrobenzaldehyde

  摘要：

  The title reaction, when carried out in carbon tetrachloride in the presence of a catalytic amount of Eu(fod)(3), leads mainly to the cis-cycloadduct 6a; the product undergoes isomerisation to its epimer 7a in the presence of the catalyst in dichloromethane.

  DOI：

  10.1016/s0040-4039(00)73430-7
• 作为产物：
  描述：

  (E)-3-(tert-butyldimethylsiloxy)-1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)buta-1,3-diene 、 对硝基苯甲醛 在 Eu(fod)3 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以34%的产率得到Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-[(2R,6S)-4-(tert-butyl-dimethyl-silanyloxy)-6-(4-nitro-phenyl)-5,6-dihydro-2H-pyran-2-yloxy]-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Hetero Diels-Alder reaction involving (E)-3-(tert-butyldimethylsiloxy)-1-(2′,3′,4′,6′-tetra- O-acetyl-β-d-glucopyranosyloxy)buta-1,3-diene and p-nitrobenzaldehyde

  摘要：

  The title reaction, when carried out in carbon tetrachloride in the presence of a catalytic amount of Eu(fod)(3), leads mainly to the cis-cycloadduct 6a; the product undergoes isomerisation to its epimer 7a in the presence of the catalyst in dichloromethane.

  DOI：

  10.1016/s0040-4039(00)73430-7