5,6-dideoxy-1,2-O-isopropylidene-3-O-(4-methoxybenzyl)-6-C-phenyl-α-D-galactofuranose | 700870-92-4

• 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: 5,6-dideoxy-1,2-O-isopropylidene-3-O-(4-methoxybenzyl)-6-C-phenyl-α-D-galactofuranose
• 英文别名: (3aR,5S,6S,6aR)-6-[(4-methoxyphenyl)methoxy]-2,2-dimethyl-5-(2-phenylethyl)-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole
• CAS: 700870-92-4
• 化学式: C₂₃H₂₈O₅
• 分子量: 384.472
• InChiKey: TXWGTKCQBAYWEV-FNAHDJPLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5,6-dideoxy-1,2-O-isopropylidene-3-O-(4-methoxybenzyl)-6-C-phenyl-α-D-galactofuranose 在 sodium periodate 、 硫酸 作用下， 以 1,4-二氧六环 、 甲醇 、 水 为溶剂， 生成 (2S,3S)-2-(4-methoxybenzyloxy)-3-formyloxy-5-phenyl-1-pentanal
  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：

  5,6-dideoxy-1,2-O-(isopropylidene)-6-phenyl-α-D-xylo-hexofuranose 在 吡啶 、 二(3-甲基丁烷-2-基)硼烷 、 四丁基碘化铵 、 sodium hydride 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 50.0h， 生成 5,6-dideoxy-1,2-O-isopropylidene-3-O-(4-methoxybenzyl)-6-C-phenyl-α-D-galactofuranose
  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

文献信息

• 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
  作者：Ravi P. Singh、Vinod K. Singh

  DOI：10.1021/jo049858n

  日期：2004.5.1

  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.