1,6-anhydro-2,3-di-O-methyl-5-C-hydroxy-4-O-benzyl-β-L-idopyranose | 1384974-88-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,6-anhydro-2,3-di-O-methyl-5-C-hydroxy-4-O-benzyl-β-L-idopyranose
• 英文别名: (1S,2S,3R,4R,5S)-3,4-dimethoxy-2-phenylmethoxy-6,8-dioxabicyclo[3.2.1]octan-1-ol
• CAS: 1384974-88-2
• 化学式: C₁₅H₂₀O₆
• 分子量: 296.32
• InChiKey: UFEXFPSQZFPKKN-MRLBHPIUSA-N

物化性质

• 熔点：
  106-108 °C(Solvent: Dichloromethane ; Hexane)
• 沸点：
  417.6±45.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,6-anhydro-2,3-di-O-methyl-5-C-hydroxy-4-O-benzyl-β-L-idopyranose 在 吡啶 、 4-二甲氨基吡啶 、 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 20.5h， 生成 1,6-anhydro-2,3-di-O-methyl-4-O-benzyl-5-C-phenyoxythiocarbonyloxy-β-L-idopyranose
  参考文献：
  名称：

  Formation of septanoses from hexopyranosides via 5,6-exo-glycals

  摘要：

  Methyl D-hexo-5-ulosides are obtained in high yield by dihydroxylation of 5,6-exo-glucal compounds. The bicyclic structure (1,6-anhydropyrano-5-ulose) of the products is adopted in solution and in solid state in a C-4(1) conformation. This methodology has been used to prepare 1,6-anhydro-L-idopyrano-5-uloses. Further manipulation of the 1,6-anhydro bridge allowed the preparation of the yet unknown septano-5-uloses in moderate to high yields. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2012.02.026
• 作为产物：
  描述：

  methyl 4-O-benzoyl-6-bromo-6-deoxy-2,3-di-O-methyl-α-D-glucopyranoside 在 potassium osmate(VI) 、 sodium methylate 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 12.0h， 生成 1,6-anhydro-2,3-di-O-methyl-5-C-hydroxy-4-O-benzyl-β-L-idopyranose
  参考文献：
  名称：

  Formation of septanoses from hexopyranosides via 5,6-exo-glycals

  摘要：

  Methyl D-hexo-5-ulosides are obtained in high yield by dihydroxylation of 5,6-exo-glucal compounds. The bicyclic structure (1,6-anhydropyrano-5-ulose) of the products is adopted in solution and in solid state in a C-4(1) conformation. This methodology has been used to prepare 1,6-anhydro-L-idopyrano-5-uloses. Further manipulation of the 1,6-anhydro bridge allowed the preparation of the yet unknown septano-5-uloses in moderate to high yields. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2012.02.026

文献信息

• Formation of septanoses from hexopyranosides via 5,6-exo-glycals
  作者：Olivier Jackowski、Françoise Chrétien、Claude Didierjean、Yves Chapleur

  DOI：10.1016/j.carres.2012.02.026

  日期：2012.7

  Methyl D-hexo-5-ulosides are obtained in high yield by dihydroxylation of 5,6-exo-glucal compounds. The bicyclic structure (1,6-anhydropyrano-5-ulose) of the products is adopted in solution and in solid state in a C-4(1) conformation. This methodology has been used to prepare 1,6-anhydro-L-idopyrano-5-uloses. Further manipulation of the 1,6-anhydro bridge allowed the preparation of the yet unknown septano-5-uloses in moderate to high yields. (C) 2012 Elsevier Ltd. All rights reserved.