(1S)-tetra-O-acetyl-1-(4-acetyl-phenyl)-1,5-anhydro-D-glucitol | 102475-76-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (1S)-tetra-O-acetyl-1-(4-acetyl-phenyl)-1,5-anhydro-D-glucitol
• 英文别名: (3R,4R,5S)-2-(acetoxymethyl)-6-(4-acetylphenyl)tetrahydro-2H-pyran-3,4,5-triyltriacetate；(1S)-tetra-O-acetyl-1-(4-acetyl-phenyl)-1,5-anhydro-D-glucitol；(1S)-Tetra-O-acetyl-1-(4-acetyl-phenyl)-1,5-anhydro-D-glucit
• CAS: 102475-76-3
• 化学式: C₂₂H₂₆O₁₀
• 分子量: 450.442
• InChiKey: WMELNZYZHDEYME-TWGBQZSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.69
• 重原子数：
  32.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  131.5
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为产物：
  描述：

  乙酰溴 、 (2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)benzene 在 三氯化铝 、 Petroleum ether 作用下， 生成 (1S)-tetra-O-acetyl-1-(4-acetyl-phenyl)-1,5-anhydro-D-glucitol
  参考文献：
  名称：

  Shdanow; Dorofeenko, Doklady Akademii Nauk SSSR, 1957, vol. 112, p. 433

  摘要：

  DOI：

文献信息

• Nickel-catalyzed reductive coupling of glucosyl halides with aryl/vinyl halides enabling β-selective preparation of C-aryl/vinyl glucosides
  作者：Jiandong Liu、Chuanhu Lei、Hegui Gong

  DOI：10.1007/s11426-019-9501-4

  日期：2019.11

  This work describes stereoselective preparation of β-C-aryl/vinyl glucosides via mild Ni-catalyzed reductive arylation and vinylation of C1-glucosyl halides with aryl and vinyl halides. A broad range of aryl halides and vinyl halides were employed to yield C-aryl/vinyl glucosides in 42%–93% yields. Good to excellent β-selectivities were obtained for C-glucosides by using tridentate ligand.

  这项工作描述了通过温和的Ni催化的还原性芳基化和C 1-葡萄糖基卤化物与芳基和乙烯基卤化物的乙烯基化，立体选择性地制备β- C-芳基/乙烯基葡糖苷。广泛使用的芳基卤化物和乙烯基卤化物可产生C-芳基/乙烯基葡糖苷，产率为42％–93％。通过使用三齿配体，对C-葡糖苷获得了良好至优异的β-选择性。
• Stereoselective Preparation of α-<i>C</i>-Vinyl/Aryl Glycosides via Nickel-Catalyzed Reductive Coupling of Glycosyl Halides with Vinyl and Aryl Halides
  作者：Jiandong Liu、Hegui Gong

  DOI：10.1021/acs.orglett.8b03567

  日期：2018.12.21

  Facile preparation of the α-C-vinyl and -aryl glycosides has been developed via mild Ni-catalyzed reductive vinylation and arylation of C1-glycosyl halides with vinyl/aryl halides. Good to high α-selectivities were achieved for C-glucosides, galactosides, maltoside, and mannosides, which were dictated by the employment of pyridine type ligands. As such, the present work represents unprecedented control

  通过温和的Ni催化还原性乙烯基化和C1-糖基卤化物与乙烯基/芳基卤化物的芳基化，已经开发出了制备α- C-乙烯基和-芳基糖苷的简便方法。对于C-葡萄糖苷，半乳​​糖苷，麦芽糖苷和甘露糖苷，具有良好或较高的α选择性，这是由吡啶类配体的使用决定的。这样，本发明代表了使用交叉偶联方法对C-乙烯基葡糖苷的高水平α-选择性的空前控制，并且通过催化剂控制的偶联策略提供了迄今为止最优化的C-芳基葡糖苷的α-选择性制备。