5,6-dideoxy-3-O-(4-methoxybenzyl)-6-C-phenyl-α-D-glucofuranose | 700870-72-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5,6-dideoxy-3-O-(4-methoxybenzyl)-6-C-phenyl-α-D-glucofuranose
• CAS: 700870-72-0
• 化学式: C₂₀H₂₄O₅
• 分子量: 344.408
• InChiKey: NGKJPGBORSLWMX-ZRNYENFQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.29
• 重原子数：
  25.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  68.15
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  5,6-dideoxy-3-O-(4-methoxybenzyl)-6-C-phenyl-α-D-glucofuranose 在 sodium periodate 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 1.67h， 生成 ethyl (4R,5R)-4-(4-methoxybenzyloxy)-5-formyloxy-7-phenyl-(2Z)-heptenoate
  参考文献：
  名称：

  Facile One-Step Synthesis of β-Alkoxy Lactone via Sequential Lactonization and 1,4-Addition of Alkoxide Group:  Total Synthesis of All Stereoisomers of Dihydrokawain-5-ol

  摘要：

  We describe here a divergent total synthesis of all of the four stereoisomers of dihydrokawain-5-ol starting from alpha-D-glucose. The approach involves the use of Ando's modification of Horner-Wadsworth-Emmons homologation to give a alpha,beta-unsaturated ester. Subsequently, lactonization and 1,4-addition of OMe group in one step provided a delta-lactone, which was converted into the target compounds in two steps.

  DOI：

  10.1021/jo049858n
• 作为产物：
  描述：

  (3aR,5R,6S,6aR)-6-(4-Methoxy-benzyloxy)-2,2-dimethyl-5-((Z)-styryl)-tetrahydro-furo[2,3-d][1,3]dioxole 在 palladium on activated charcoal 硫酸 、 氢气 作用下， 以 1,4-二氧六环 、 乙醇 、 水 为溶剂， 20.0~50.0 ℃ 、101.33 kPa 条件下， 反应 8.0h， 生成 5,6-dideoxy-3-O-(4-methoxybenzyl)-6-C-phenyl-α-D-glucofuranose
  参考文献：
  名称：

  Facile One-Step Synthesis of β-Alkoxy Lactone via Sequential Lactonization and 1,4-Addition of Alkoxide Group:  Total Synthesis of All Stereoisomers of Dihydrokawain-5-ol

  摘要：

  We describe here a divergent total synthesis of all of the four stereoisomers of dihydrokawain-5-ol starting from alpha-D-glucose. The approach involves the use of Ando's modification of Horner-Wadsworth-Emmons homologation to give a alpha,beta-unsaturated ester. Subsequently, lactonization and 1,4-addition of OMe group in one step provided a delta-lactone, which was converted into the target compounds in two steps.

  DOI：

  10.1021/jo049858n