6-methoxy-4-phenoxymethyl-3,6-dihydropyran-2,2-dicarboxylic acid diethyl ester

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 6-methoxy-4-phenoxymethyl-3,6-dihydropyran-2,2-dicarboxylic acid diethyl ester
• 英文别名: Diethyl 2-methoxy-4-(phenoxymethyl)-2,5-dihydropyran-6,6-dicarboxylate
• 化学式: C₁₉H₂₄O₇
• 分子量: 364.395
• InChiKey: ZIBGWKOOVKPVSN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  [(E)-4-methoxy-2-methylidenebut-3-enoxy]benzene 、 酮基丙二酸二乙酯 在 对苯二酚 作用下， 以 四氢呋喃 为溶剂， 反应 72.0h， 以94%的产率得到6-methoxy-4-phenoxymethyl-3,6-dihydropyran-2,2-dicarboxylic acid diethyl ester
  参考文献：
  名称：

  Thermal/Hyperbaric Heterocycloaddition of 1,4-Dialkoxy-1,3-dienes:  The de novo (E,Z) Way to Sugars

  摘要：

  1-(Z)-Alkoxy-4-(E)-methoxybutadiene derivatives have been reacted with ethylgyoxylate and diethyl ketomalonate under thermal or hyperbaric conditions. They provide, with a total regioselectivity and fair to total endoselectivities, the expected dihydropyranic cycloadducts. Three of those pseudoglycals have been converted in a few classical steps (deprotection, reduction, and dihydroxylation) into (racemic) allose, mannose, and gullose derivatives. The order of these three steps has a direct influence on the efficiency of the transformation and determines the stereochemistry of the final sugar.

  DOI：

  10.1021/jo0204193

文献信息

• Thermal/Hyperbaric Heterocycloaddition of 1,4-Dialkoxy-1,3-dienes:  The <i>de novo</i> (<i>E</i>,<i>Z</i>) Way to Sugars
  作者：Carole Bataille、Gautier Bégin、Anne Guillam、Loïc Lemiègre、Caroline Lys、Jacques Maddaluno、Loïc Toupet

  DOI：10.1021/jo0204193

  日期：2002.11.1

  1-(Z)-Alkoxy-4-(E)-methoxybutadiene derivatives have been reacted with ethylgyoxylate and diethyl ketomalonate under thermal or hyperbaric conditions. They provide, with a total regioselectivity and fair to total endoselectivities, the expected dihydropyranic cycloadducts. Three of those pseudoglycals have been converted in a few classical steps (deprotection, reduction, and dihydroxylation) into (racemic) allose, mannose, and gullose derivatives. The order of these three steps has a direct influence on the efficiency of the transformation and determines the stereochemistry of the final sugar.