(2R,3R,4S)-3-(3,4,5-trimethoxybenzyl)-4-(3,4,5-trimethoxyphenyl)-2-((R)-4-ethyl-2-oxo-oxazolidin-3-yl)-3,4-dihydro-2H-pyran-6-carboxylic acid methyl ester | 1296671-54-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2R,3R,4S)-3-(3,4,5-trimethoxybenzyl)-4-(3,4,5-trimethoxyphenyl)-2-((R)-4-ethyl-2-oxo-oxazolidin-3-yl)-3,4-dihydro-2H-pyran-6-carboxylic acid methyl ester
• 英文别名: methyl (2R,3R,4S)-2-[(4R)-4-ethyl-2-oxo-1,3-oxazolidin-3-yl]-4-(3,4,5-trimethoxyphenyl)-3-[(3,4,5-trimethoxyphenyl)methyl]-3,4-dihydro-2H-pyran-6-carboxylate
• CAS: 1296671-54-9
• 化学式: C₃₁H₃₉NO₁₁
• 分子量: 601.651
• InChiKey: UETGQXZFVIGFAO-QFIBFXAGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  43
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  120
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S)-3-(3,4,5-trimethoxybenzyl)-4-(3,4,5-trimethoxyphenyl)-2-((R)-4-ethyl-2-oxo-oxazolidin-3-yl)-3,4-dihydro-2H-pyran-6-carboxylic acid methyl ester 在 三氟甲磺酸 、 三氟甲磺酸酐 、 三氟化硼乙醚 、 manganese triacetate 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以32%的产率得到(8R,8aR,4bS,13aR)-8-((R)-4-ethyl-2-oxo-oxazolidin-3-yl)-4b,8,8a,9-tetrahydro-1,2,3,11,12,13-hexamethoxy-7-oxa-tribenzo[a,c,e]cycloheptene-6-carboxylic acid methyl ester
  参考文献：
  名称：

  New two-step sequence involving a hetero-Diels–Alder and a nonphenolic oxidative coupling reaction: a convergent access to analogs of steganacin

  摘要：

  A new family of analogs of steganacin, an important antimitotic compound, was accessed. It takes advantage of a completely stereoselective sequence of two key steps. The central dihydropyrane core is built by a highly diastereoselective and facially controlled hetero-Diels-Alder reaction. It is followed by a nonphenolic biaryl oxidative coupling with a complete atropo-stereoselectivity. It leads to a quick way to form cyclic biaryl lignans. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.01.097
• 作为产物：
  描述：

  3-(3,4,5-三甲氧基苯基)-1-丙醇 在 tris(6,6,7,7,8,8-heptafluoro-2,2-dimethyl-3,5-octadionato)europium(III) 、 对甲苯磺酸 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 环己烷 、 甲苯 为溶剂， 反应 175.0h， 生成 (2R,3R,4S)-3-(3,4,5-trimethoxybenzyl)-4-(3,4,5-trimethoxyphenyl)-2-((R)-4-ethyl-2-oxo-oxazolidin-3-yl)-3,4-dihydro-2H-pyran-6-carboxylic acid methyl ester
  参考文献：
  名称：

  New two-step sequence involving a hetero-Diels–Alder and a nonphenolic oxidative coupling reaction: a convergent access to analogs of steganacin

  摘要：

  A new family of analogs of steganacin, an important antimitotic compound, was accessed. It takes advantage of a completely stereoselective sequence of two key steps. The central dihydropyrane core is built by a highly diastereoselective and facially controlled hetero-Diels-Alder reaction. It is followed by a nonphenolic biaryl oxidative coupling with a complete atropo-stereoselectivity. It leads to a quick way to form cyclic biaryl lignans. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.01.097

文献信息

• New two-step sequence involving a hetero-Diels–Alder and a nonphenolic oxidative coupling reaction: a convergent access to analogs of steganacin
  作者：Mathieu Y. Laurent、Vivien Stocker、Valéry Momo Temgoua、Gilles Dujardin、Robert Dhal

  DOI：10.1016/j.tetlet.2011.01.097

  日期：2011.4

  A new family of analogs of steganacin, an important antimitotic compound, was accessed. It takes advantage of a completely stereoselective sequence of two key steps. The central dihydropyrane core is built by a highly diastereoselective and facially controlled hetero-Diels-Alder reaction. It is followed by a nonphenolic biaryl oxidative coupling with a complete atropo-stereoselectivity. It leads to a quick way to form cyclic biaryl lignans. (C) 2011 Elsevier Ltd. All rights reserved.