Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-[(2S,6S)-4-(tert-butyl-dimethyl-silanyloxy)-6-(4-nitro-phenyl)-5,6-dihydro-2H-pyran-2-yloxy]-tetrahydro-pyran-4-yl ester | 162181-12-6

• 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-[(2S,6S)-4-(tert-butyl-dimethyl-silanyloxy)-6-(4-nitro-phenyl)-5,6-dihydro-2H-pyran-2-yloxy]-tetrahydro-pyran-4-yl ester
• 英文别名: [(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-[[(2S,6S)-4-[tert-butyl(dimethyl)silyl]oxy-2-(4-nitrophenyl)-3,6-dihydro-2H-pyran-6-yl]oxy]oxan-2-yl]methyl acetate
• CAS: 162181-12-6
• 化学式: C₃₁H₄₃NO₁₄Si
• 分子量: 681.766
• InChiKey: UVSSLJSITVQSNA-AHRBKPOASA-N

物化性质

• 沸点：
  669.6±55.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.39
• 重原子数：
  47
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  188
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-[(2S,6S)-4-(tert-butyl-dimethyl-silanyloxy)-6-(4-nitro-phenyl)-5,6-dihydro-2H-pyran-2-yloxy]-tetrahydro-pyran-4-yl ester 在 sodium tetrahydroborate 、 四氧化锇 、 cerium(III) chloride 、 barium chlorate 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 14.5h， 生成 (3R,4S,6S)-4-(tert-Butyl-dimethyl-silanyloxy)-6-(4-nitro-phenyl)-tetrahydro-pyran-2,3-diol
  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：

  (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