4-O-Benzoyl-2,3-di-O-benzyl-α-L-fucopyranosyl trichloroacetimidate | 1607433-68-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-O-Benzoyl-2,3-di-O-benzyl-α-L-fucopyranosyl trichloroacetimidate
• 英文别名: Bn(-2)[Bn(-3)][Bz(-4)]Fuc(a)-O-C(NH)CCl3；[(2S,3R,4R,5S,6S)-2-methyl-4,5-bis(phenylmethoxy)-6-(2,2,2-trichloroethanimidoyl)oxyoxan-3-yl] benzoate
• CAS: 1607433-68-0
• 化学式: C₂₉H₂₈Cl₃NO₆
• 分子量: 592.903
• InChiKey: RBWXWQOXQQLYEF-QVNAIVNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  39
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  87.1
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-O-Benzoyl-2,3-di-O-benzyl-α-L-fucopyranosyl trichloroacetimidate 、 p-tolyl 4-O-benzoyl-2-O-benzyl-1-thio-β-L-fucopyranoside 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 1.83h， 以67%的产率得到p-Tolyl (4-O-benzoyl-2,3-di-O-benzyl-α-L-fucopyranosyl)-(1→ 3)-4-O-benzoyl-2-O-benzyl-1-thio-β-L-fucopyranoside
  参考文献：
  名称：

  Stereoselective Synthesis of a Sulfated Tetrasaccharide Corresponding to a Rare Sequence in the Galactofucan Isolated from Sargassum polycystum

  摘要：

  The first chemical synthesis of a highly sulfated tetrasaccharide 1, as the rare sequence in the galactofucan isolated from the brown alga Sargassum polycystum, was achieved in a convergent and stereoselective manner. The key features of the synthetic strategy include construction of multiple contiguous 1,2-cis glycosidic bonds and [2 + 2] assembly based on the rationally developed D-galactose building block 6. The synthesized oligosaccharides were fully characterized using a combination of coupled-HSQC and other 2D NMR techniques.

  DOI：

  10.1021/jo500503r
• 作为产物：
  描述：

  三氯乙腈 、 2,3-di-O-benzyl-4-O-benzoyl-6-deoxy-α/β-L-galactopyranose 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以75%的产率得到4-O-Benzoyl-2,3-di-O-benzyl-α-L-fucopyranosyl trichloroacetimidate
  参考文献：
  名称：

  Stereoselective Synthesis of a Sulfated Tetrasaccharide Corresponding to a Rare Sequence in the Galactofucan Isolated from Sargassum polycystum

  摘要：

  The first chemical synthesis of a highly sulfated tetrasaccharide 1, as the rare sequence in the galactofucan isolated from the brown alga Sargassum polycystum, was achieved in a convergent and stereoselective manner. The key features of the synthetic strategy include construction of multiple contiguous 1,2-cis glycosidic bonds and [2 + 2] assembly based on the rationally developed D-galactose building block 6. The synthesized oligosaccharides were fully characterized using a combination of coupled-HSQC and other 2D NMR techniques.

  DOI：

  10.1021/jo500503r

文献信息

• Stereoselective Synthesis of a Sulfated Tetrasaccharide Corresponding to a Rare Sequence in the Galactofucan Isolated from <i>Sargassum polycystum</i>
  作者：Jun Zhou、Liping Yang、Wenhao Hu

  DOI：10.1021/jo500503r

  日期：2014.5.16

  The first chemical synthesis of a highly sulfated tetrasaccharide 1, as the rare sequence in the galactofucan isolated from the brown alga Sargassum polycystum, was achieved in a convergent and stereoselective manner. The key features of the synthetic strategy include construction of multiple contiguous 1,2-cis glycosidic bonds and [2 + 2] assembly based on the rationally developed D-galactose building block 6. The synthesized oligosaccharides were fully characterized using a combination of coupled-HSQC and other 2D NMR techniques.