(E)-3-[3-Benzyloxy-4-((3aR,4S,6R,7S,7aS)-7-hydroxy-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-phenyl]-acrylic acid methyl ester | 868671-99-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-3-[3-Benzyloxy-4-((3aR,4S,6R,7S,7aS)-7-hydroxy-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-phenyl]-acrylic acid methyl ester
• CAS: 868671-99-2
• 化学式: C₂₆H₃₀O₈
• 分子量: 470.519
• InChiKey: RDFUPUZRLWZDMM-LJEXBKOXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.46
• 重原子数：
  34.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  92.68
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (E)-3-[3-Benzyloxy-4-((3aR,4S,6R,7S,7aS)-7-hydroxy-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-phenyl]-acrylic acid methyl ester 在 吡啶 、 pyridine-SO3 complex 作用下， 反应 1.5h， 以91%的产率得到(E)-3-[3-Benzyloxy-4-((3aR,4S,6R,7S,7aR)-2,2,4-trimethyl-7-sulfooxy-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-phenyl]-acrylic acid methyl ester
  参考文献：
  名称：

  Synthesis of the Saccharomicin Fucose−Aglycon Conjugate and Determination of Absolute Configuration

  摘要：

  Schmidt glycosylation of the appropriately protected 3,4-dihydroxycinnamate methyl ester with 2,3,4-triacetoxyfucopyranosyltrichloroacetimidate gives aryl glycoside in high yield and diastereoselectivity. 2-Sulfation of fucose, installation of taurine, and global deprotection of the remaining protecting groups affords the fucose-aglycon conjugate of saccharomicin. This synthesis which arises from L-fucose also establishes the absolute configuration of the reducing terminus of the saccharomicin oligosaccharide.

  DOI：

  10.1021/ol051971s
• 作为产物：
  描述：

  4-羟基 3-(苯基甲氧基)苯甲醛 在 4 A molecular sieve 、 三氟化硼乙醚 、 4-甲基苯磺酸吡啶 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 、 甲苯 为溶剂， 反应 42.5h， 生成 (E)-3-[3-Benzyloxy-4-((3aR,4S,6R,7S,7aS)-7-hydroxy-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-phenyl]-acrylic acid methyl ester
  参考文献：
  名称：

  Synthesis of the Saccharomicin Fucose−Aglycon Conjugate and Determination of Absolute Configuration

  摘要：

  Schmidt glycosylation of the appropriately protected 3,4-dihydroxycinnamate methyl ester with 2,3,4-triacetoxyfucopyranosyltrichloroacetimidate gives aryl glycoside in high yield and diastereoselectivity. 2-Sulfation of fucose, installation of taurine, and global deprotection of the remaining protecting groups affords the fucose-aglycon conjugate of saccharomicin. This synthesis which arises from L-fucose also establishes the absolute configuration of the reducing terminus of the saccharomicin oligosaccharide.

  DOI：

  10.1021/ol051971s