(2R,3S,4S)-3-Allyloxy-2-allyloxymethyl-4-furan-2-yl-3,4-dihydro-2H-pyran

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: (2R,3S,4S)-3-Allyloxy-2-allyloxymethyl-4-furan-2-yl-3,4-dihydro-2H-pyran
• 英文别名: (2R,3S,4S)-4-(furan-2-yl)-3-prop-2-enoxy-2-(prop-2-enoxymethyl)-3,4-dihydro-2H-pyran
• 化学式: C₁₆H₂₀O₄
• 分子量: 276.332
• InChiKey: BIKCFEFDTCENFP-BMFZPTHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  40.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  呋喃 、 3,4,6-tri-O-allyl-D-glucal 在 indium(III) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以84%的产率得到(2R,3S,4S)-3-Allyloxy-2-allyloxymethyl-4-furan-2-yl-3,4-dihydro-2H-pyran
  参考文献：
  名称：

  InCl3-catalyzed stereoselective synthesis of C-glycosyl heteroaromatics

  摘要：

  Glycals react smoothly with furan in the presence of a catalytic temperature amount of indium trichloride at ambient to afford predominantly the C-3-substituted glycals in high yields. Other heteroaromatics including 2-benzyloxymethylfuran. thiophene and N-Boc protected indole afford exclusively C-I-glycosides in good yields with high beta-selectivity under similar reaction conditions. (C) 2002 Elsevier Science Ltd. All rights reserved,

  DOI：

  10.1016/s0040-4039(02)00187-9

文献信息

• InCl3-catalyzed stereoselective synthesis of C-glycosyl heteroaromatics
  作者：J.S Yadav、B.V.S Reddy、J.V Raman、N Niranjan、S Kiran Kumar、A.C Kunwar

  DOI：10.1016/s0040-4039(02)00187-9

  日期：2002.3

  Glycals react smoothly with furan in the presence of a catalytic temperature amount of indium trichloride at ambient to afford predominantly the C-3-substituted glycals in high yields. Other heteroaromatics including 2-benzyloxymethylfuran. thiophene and N-Boc protected indole afford exclusively C-I-glycosides in good yields with high beta-selectivity under similar reaction conditions. (C) 2002 Elsevier Science Ltd. All rights reserved,