Allyl-[(S)-1-((3aS,5S,6R,6aS)-6-benzyloxy-3a-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-allyl]-amine | 606970-46-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Allyl-[(S)-1-((3aS,5S,6R,6aS)-6-benzyloxy-3a-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-allyl]-amine
• CAS: 606970-46-1
• 化学式: C₂₈H₃₅NO₅
• 分子量: 465.59
• InChiKey: HSFNAZCUFZROGN-HIBXFOCJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.37
• 重原子数：
  34.0
• 可旋转键数：
  12.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  58.18
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  Allyl-[(S)-1-((3aS,5S,6R,6aS)-6-benzyloxy-3a-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-allyl]-amine 在 四(三苯基膦)钯 1,3-二甲基巴比妥酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以80%的产率得到(S)-1-((3aS,5S,6R,6aS)-6-Benzyloxy-3a-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-allylamine
  参考文献：
  名称：

  General Access to Iminosugar C-Glycoside Building Blocks by Means of Cross-Metathesis:  A Gateway to Glycoconjugate Mimetics

  摘要：

  [GRAPHICS]Cross-metathesis reactions of alpha-1-C-allyl-1-deoxynojirimycin derivatives 7a,b and various functionalized alkenes mediated by Grubbs's catalyst 3 are reported. The reactions showed reasonable to very good yields and excellent E/Z selectivity. This methodology allows the efficient and convergent synthesis of iminosugar C-glycosides with a great degree of structural diversity in the aglycone, opening the way to a variety of new glycoconjugate mimetics of biological interest.

  DOI：

  10.1021/ol035117h
• 作为产物：
  描述：

  3,6-di-O-benzyl-4,5-O-isopropylidene-D-xylo-aldehydo-hexos-5-ulo-2,5-furanose 以 乙醚 、 二氯甲烷 为溶剂， 反应 26.0h， 生成 Allyl-[(S)-1-((3aS,5S,6R,6aS)-6-benzyloxy-3a-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-allyl]-amine
  参考文献：
  名称：

  General Access to Iminosugar C-Glycoside Building Blocks by Means of Cross-Metathesis:  A Gateway to Glycoconjugate Mimetics

  摘要：

  [GRAPHICS]Cross-metathesis reactions of alpha-1-C-allyl-1-deoxynojirimycin derivatives 7a,b and various functionalized alkenes mediated by Grubbs's catalyst 3 are reported. The reactions showed reasonable to very good yields and excellent E/Z selectivity. This methodology allows the efficient and convergent synthesis of iminosugar C-glycosides with a great degree of structural diversity in the aglycone, opening the way to a variety of new glycoconjugate mimetics of biological interest.

  DOI：

  10.1021/ol035117h