(4S,5R,6R)-methyl 5-((benzo[d][1,3]dioxol-5-yl)methyl)-6-((4R)-4-ethyl-2-oxo-1,3-oxazolidin-3-yl)-5,6-dihydro-4-(3,4,5-trimethoxyphenyl)-5-phenyl-4H-pyran-2-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: (4S,5R,6R)-methyl 5-((benzo[d][1,3]dioxol-5-yl)methyl)-6-((4R)-4-ethyl-2-oxo-1,3-oxazolidin-3-yl)-5,6-dihydro-4-(3,4,5-trimethoxyphenyl)-5-phenyl-4H-pyran-2-carboxylate
• 英文别名: (2R,3R,4S)-3-(benzo[d][1,3]dioxol-5-ylmethyl)-2-((R)-4-ethyl-2-oxo-oxazolidin-3-yl)-4-(3,4,5-trimethoxyphenyl)-3,4-dihydro-2H-pyran-6-carboxylic acid methyl ester；methyl (2R,3R,4S)-3-(1,3-benzodioxol-5-ylmethyl)-2-[(4R)-4-ethyl-2-oxo-1,3-oxazolidin-3-yl]-4-(3,4,5-trimethoxyphenyl)-3,4-dihydro-2H-pyran-6-carboxylate
• 化学式: C₂₉H₃₃NO₁₀
• 分子量: 555.582
• InChiKey: AOHKQLFFEJDGEC-MMCDXOEFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  40
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  111
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (4S,5R,6R)-methyl 5-((benzo[d][1,3]dioxol-5-yl)methyl)-6-((4R)-4-ethyl-2-oxo-1,3-oxazolidin-3-yl)-5,6-dihydro-4-(3,4,5-trimethoxyphenyl)-5-phenyl-4H-pyran-2-carboxylate 在 thallium (III) oxide 、 三氟甲磺酸 、 三氟甲磺酸酐 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以62%的产率得到(8R,8aR,4bS,13aS)-8-((R)-4-ethyl-2-oxo-oxazolidin-3-yl)-4b,8,8a,9-tetrahydro-1,2,3-trimethoxy-11,12-methylenedioxy-7-oxa-tribenzo[a,c,e]cyclo-heptene-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：

  3,4-methylenedioxy-trans-cinnamic acid 在 lithium aluminium tetrahydride 、 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 四氢呋喃 、 二氯甲烷 、 环己烷 、 甲苯 为溶剂， 反应 175.0h， 生成 (4S,5R,6R)-methyl 5-((benzo[d][1,3]dioxol-5-yl)methyl)-6-((4R)-4-ethyl-2-oxo-1,3-oxazolidin-3-yl)-5,6-dihydro-4-(3,4,5-trimethoxyphenyl)-5-phenyl-4H-pyran-2-carboxylate
  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

• Lewis Acid Tuned Facial Stereodivergent HDA Reactions Using β-Substituted <i>N</i>-Vinyloxazolidinones
  作者：Frédéric Gohier、Keltoum Bouhadjera、Djibril Faye、Catherine Gaulon、Vincent Maisonneuve、Gilles Dujardin、Robert Dhal

  DOI：10.1021/ol062626l

  日期：2007.1.1

  R' = Me, Ar, CH2 Ar) and beta,gamma-unsaturated alpha-ketoesters (R = Ar) afforded heteroadducts with high levels of endo and facial selectivities. A complete reversal of facial differentiation was achieved by varying the Lewis acid, leading to the stereoselective formation of either endo-alpha or endo-beta adducts. [reaction: see text].

  新的β-取代的N-乙烯基-1,3-恶唑烷-2-酮（具有R'= Me，Ar，CH2 Ar）与β，γ-不饱和α-酮酸酯（[4 + 2]酸催化的杂环加成）之间（ R = Ar）提供具有高水平的内和面选择性的杂加合物。通过改变路易斯酸可以完全逆转面部分化，从而导致内-α或内-β加合物的立体选择性形成。[反应：请参见文字]。
• 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.