5,6-dideoxy-1,2-O-(isopropylidene)-3-O-(4-methoxybenzyl)-6-phenyl-α-D-ribo-hexofuranose | 700870-83-3

• 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-phenyl-α-D-ribo-hexofuranose
• CAS: 700870-83-3
• 化学式: C₂₃H₂₈O₅
• 分子量: 384.472
• InChiKey: TXWGTKCQBAYWEV-GXRSIYKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.09
• 重原子数：
  28.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  46.15
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  5,6-dideoxy-1,2-O-(isopropylidene)-3-O-(4-methoxybenzyl)-6-phenyl-α-D-ribo-hexofuranose 在 硫酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 以69%的产率得到5,6-dideoxy-3-O-(4-methoxybenzyl)-6-phenyl-D-ribo-hexofuranose
  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)-2,2-dimethyl-5-(2-phenylethyl)-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole 在 palladium on activated charcoal sodium tetrahydroborate 、 草酰氯 、 氢气 、 四丁基碘化铵 、 sodium hydride 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 28.0h， 生成 5,6-dideoxy-1,2-O-(isopropylidene)-3-O-(4-methoxybenzyl)-6-phenyl-α-D-ribo-hexofuranose
  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