5-O-β-D-glucopyranosylisosorbide | 795279-96-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-O-β-D-glucopyranosylisosorbide
• 英文别名: (2S,3R,4S,5S,6R)-2-[[(3S,3aR,6R,6aR)-3-hydroxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-6-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 795279-96-8
• 化学式: C₁₂H₂₀O₉
• 分子量: 308.285
• InChiKey: GDHQCLLVAPSOTN-SNPVHUDHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  138
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  苯甲酰氯 、 5-O-β-D-glucopyranosylisosorbide 在 吡啶 作用下， 以 苯 为溶剂， 以65%的产率得到2-O-benzoyl-5-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)isosorbide
  参考文献：
  名称：

  Glycosylation of l,4:3,6-dianhydro-d-glucitol (isosorbide)

  摘要：

  Condensation of 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl-, 2,3,4-tri-O-acetyl-alpha-D-xylopyranosyl- and of 2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranosyl bromides with 1,4:3,6-dianhydro-D-glucitol under Koenigs-Knorr conditions, and using the Helferich modification of the reaction showed regioselectivity in glysosylation at C-5 of isosorbide. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.07.007
• 作为产物：
  描述：

  异山梨醇 在 sodium methylate 、 silver(l) oxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 42.0h， 生成 5-O-β-D-glucopyranosylisosorbide
  参考文献：
  名称：

  Glycosylation of l,4:3,6-dianhydro-d-glucitol (isosorbide)

  摘要：

  Condensation of 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl-, 2,3,4-tri-O-acetyl-alpha-D-xylopyranosyl- and of 2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranosyl bromides with 1,4:3,6-dianhydro-D-glucitol under Koenigs-Knorr conditions, and using the Helferich modification of the reaction showed regioselectivity in glysosylation at C-5 of isosorbide. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.07.007

文献信息

• Glycosylation of l,4:3,6-dianhydro-d-glucitol (isosorbide)
  作者：David J. Claffey、Mary F. Casey、Patrick A. Finan

  DOI：10.1016/j.carres.2004.07.007

  日期：2004.10

  Condensation of 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl-, 2,3,4-tri-O-acetyl-alpha-D-xylopyranosyl- and of 2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranosyl bromides with 1,4:3,6-dianhydro-D-glucitol under Koenigs-Knorr conditions, and using the Helferich modification of the reaction showed regioselectivity in glysosylation at C-5 of isosorbide. (C) 2004 Elsevier Ltd. All rights reserved.