2-hydroxymethyl-6-methoxy-3,6-dihydro-2H-pyran-3-ol | 6605-30-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 2-hydroxymethyl-6-methoxy-3,6-dihydro-2H-pyran-3-ol
• 英文别名: (2S,3R,6S)-2-(hydroxymethyl)-6-methoxy-3,6-dihydro-2H-pyran-3-ol
• CAS: 6605-30-7；22860-25-9；23339-19-7；33647-97-1；62279-47-4；62279-48-5
• 化学式: C₇H₁₂O₄
• 分子量: 160.17
• InChiKey: BDSSJXGPGYQORZ-VQVTYTSYSA-N

物化性质

• 沸点：
  305.9±42.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  E-4-bromobut-2-enal dimethyl acetal 在 lithium aluminium tetrahydride 、 叔丁基锂 、 potassium hydride 、 对苯二酚 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 、 甲苯 为溶剂， -45.0~50.0 ℃ 、1200.02 MPa 条件下， 反应 28.5h， 生成 2-hydroxymethyl-6-methoxy-3,6-dihydro-2H-pyran-3-ol
  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.