1,5-anhydro-2,3-di-O-methyl-4-O-benzyl-D-glucitol | 1384974-99-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,5-anhydro-2,3-di-O-methyl-4-O-benzyl-D-glucitol
• CAS: 1384974-99-5
• 化学式: C₁₅H₂₂O₅
• 分子量: 282.337
• InChiKey: DBGIXFQLMYYKEN-LXTVHRRPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.99
• 重原子数：
  20.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  57.15
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1,5-anhydro-2,3-di-O-methyl-4-O-benzyl-D-glucitol 、 乙酸酐 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以85%的产率得到6-O-acetyl-1,5-anhydro-2,3-di-O-methyl-4-O-benzyl-D-glucitol
  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：

  1,6-anhydro-2,3-di-O-methyl-4-O-benzyl-5-C-phenyoxythiocarbonyloxy-β-L-idopyranose 在 三乙基硅烷 、 偶氮二异丁腈 、 三氟化硼乙醚 、 三正丁基氢锡 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 1.0h， 生成 1,5-anhydro-2,3-di-O-methyl-4-O-benzyl-D-glucitol
  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