(E)-3-(tert-butyldimethylsiloxy)-1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)buta-1,3-diene | 126025-77-2

• 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: (E)-3-(tert-butyldimethylsiloxy)-1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)buta-1,3-diene
• 英文别名: [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[(1E)-3-[tert-butyl(dimethyl)silyl]oxybuta-1,3-dienoxy]oxan-2-yl]methyl acetate
• CAS: 126025-77-2
• 化学式: C₂₄H₃₈O₁₁Si
• 分子量: 530.645
• InChiKey: HFIPQSXCGJTBBI-WXONXQOXSA-N

物化性质

• 沸点：
  545.7±50.0 °C(predicted)
• 密度：
  1.15±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.14
• 重原子数：
  36
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  133
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  4-苯基-1,2,4-三唑啉-3,5-二酮 、 (E)-3-(tert-butyldimethylsiloxy)-1-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)buta-1,3-diene 以 二氯甲烷 为溶剂， 以45%的产率得到Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(S)-7-(tert-butyl-dimethyl-silanyloxy)-1,3-dioxo-2-phenyl-2,3,5,8-tetrahydro-1H-[1,2,4]triazolo[1,2-a]pyridazin-5-yloxy]-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  Enhanced discrimination by aza dienophiles over their olefinic counterparts for the diastereotopic faces of methyl (E,E)-5-(2′,3′,4′,6′-tetra-O-acetyl-β-d-glucopyranosyloxy)penta-2,4-dienoate

  摘要：

  The title diene displays a notably higher diastereofacial selectivity towards 4-phenyl-1,2,4-triazoline-3,5-dione, pyridazine3,6-dione and phthalazine-1,4-dione than toward N-phenylmaleimide, 1,4-benzoquinone and 1,4 naphthoquinone.

  DOI：

  10.1016/s0040-4039(00)76918-8
• 作为产物：
  描述：

  (E)-4-(2',3',4',6'-Tetra-O-acetyl-β-D-glucopyranosyloxy)but-3-en-2-one 、 叔丁基二甲硅基三氟甲磺酸酯 以89%的产率得到
  参考文献：
  名称：

  LARSEN, DAVID S.;STOODLEY, RICHARD J., J. CHEM. SOC. PERKIN. TRANS. PT 1,(1989) N0, C. 1841-1852

  摘要：

  DOI：

文献信息

• Asymmetric synthesis of (5S)-4-deoxy-5-C-(4-nitrophenyl)-l-threo-pentose and (5R)-5-C-(4-nitrophenyl)-l-arabinose
  作者：Madeleine Helliwell、Iain M. Phillips、Robin G. Pritchard、Richard J. Stoodley

  DOI：10.1016/s0040-4039(99)01832-8

  日期：1999.12

  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.
• 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
  作者：Richard F. Lowe、Richard J. Stoodley

  DOI：10.1016/s0040-4039(00)73430-7

  日期：1994.8

  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.