Acetic acid (2R,3S,6S)-4-(tert-butyl-dimethyl-silanyloxy)-2-(4-nitro-phenyl)-6-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-3,6-dihydro-2H-pyran-3-yl ester | 255912-51-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Acetic acid (2R,3S,6S)-4-(tert-butyl-dimethyl-silanyloxy)-2-(4-nitro-phenyl)-6-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-3,6-dihydro-2H-pyran-3-yl ester
• 英文别名: [(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-[[(2R,3S,6S)-3-acetyloxy-4-[tert-butyl(dimethyl)silyl]oxy-2-(4-nitrophenyl)-3,6-dihydro-2H-pyran-6-yl]oxy]oxan-2-yl]methyl acetate
• CAS: 255912-51-7
• 化学式: C₃₃H₄₅NO₁₆Si
• 分子量: 739.803
• InChiKey: CSKZFOJGBOVEOB-ANUKDGBQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.93
• 重原子数：
  51
• 可旋转键数：
  17
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  214
• 氢给体数：
  0
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3S,6S)-4-(tert-butyl-dimethyl-silanyloxy)-2-(4-nitro-phenyl)-6-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-3,6-dihydro-2H-pyran-3-yl ester 以 三氟乙酸 为溶剂， 以84%的产率得到Acetic acid (2R,3S)-2-(4-nitro-phenyl)-4-oxo-3,4-dihydro-2H-pyran-3-yl ester
  参考文献：
  名称：

  Asymmetric synthesis of (5S)-4-deoxy-5-C-(4-nitrophenyl)-l-threo-pentose and (5R)-5-C-(4-nitrophenyl)-l-arabinose

  摘要：

  In the presence of Eu(fod)(3), (1E)-(2',3',4',6'-tetra-O-acetyl-beta-D-glucopyranosyloxy)buta-1,3-diene and its (3Z)-4-O-acetyl derivative undergo Re-face and endo selective hetero Diels-Alder reactions with 4-nitrobenzaldehyde, 5-nitrofuran-2-carbaldehyde and 5-nitrothiophene-2-carbaldehyde. The cycloadducts are converted into the title compounds, early examples of 'free' 5-C-arylpentopyranoses. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01832-8
• 作为产物：
  描述：

  对硝基苯甲醛 、 [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[(1E,3Z)-4-acetyloxy-3-[tert-butyl(dimethyl)silyl]oxybuta-1,3-dienoxy]oxan-2-yl]methyl acetate 在 Eu(fod)3 作用下， 以 四氯化碳 为溶剂， 以45%的产率得到Acetic acid (2R,3S,6S)-4-(tert-butyl-dimethyl-silanyloxy)-2-(4-nitro-phenyl)-6-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-3,6-dihydro-2H-pyran-3-yl ester
  参考文献：
  名称：

  Asymmetric synthesis of (5S)-4-deoxy-5-C-(4-nitrophenyl)-l-threo-pentose and (5R)-5-C-(4-nitrophenyl)-l-arabinose

  摘要：

  In the presence of Eu(fod)(3), (1E)-(2',3',4',6'-tetra-O-acetyl-beta-D-glucopyranosyloxy)buta-1,3-diene and its (3Z)-4-O-acetyl derivative undergo Re-face and endo selective hetero Diels-Alder reactions with 4-nitrobenzaldehyde, 5-nitrofuran-2-carbaldehyde and 5-nitrothiophene-2-carbaldehyde. The cycloadducts are converted into the title compounds, early examples of 'free' 5-C-arylpentopyranoses. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01832-8