2,3-di-O-benzyl-5-eno-β-D-methyl galactofuranose | 1370711-56-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3-di-O-benzyl-5-eno-β-D-methyl galactofuranose
• CAS: 1370711-56-0
• 化学式: C₂₁H₂₄O₄
• 分子量: 340.419
• InChiKey: TWSUSLDAVUTAMW-UWHLTILDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.71
• 重原子数：
  25.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2,3-di-O-benzyl-5-eno-β-D-methyl galactofuranose 在 吡啶 、 (S,S)-(+)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminocobalt(II) 、 20 wt.% Pd(OH)2 on activated carbon 、 水 、 氢气 、 溶剂黄146 、 triethylamine tris(hydrogen fluoride) 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 147.08h， 生成 2,3,5-tri-O-benzoyl-6-deoxy-6-fluoro-β-D-methyl galactofuranose
  参考文献：
  名称：

  Fluorosugar Chain Termination Agents as Probes of the Sequence Specificity of a Carbohydrate Polymerase

  摘要：

  Naturally occurring carbohydrate polymers are ubiquitous. They are assembled by polymerizing glycosyltransferases, which can generate polysaccharide products with repeating sequence patterns. The fidelity of enzymes of this class is unknown. We report a method for testing the fidelity of carbohydrate polymerase pattern deposition: we synthesized fluorosugar donors and used them as chain termination agents. The requisite nucleotide fluorosugars could be produced from a single intermediate using the Jacobsen catalyst in a kinetically controlled separation of diastereomers. The resulting fluorosugar donors were used by the galactofuranosyltransferase GlfT2 from Mycobacterium tuberculosis, and the data indicate that this enzyme mediates the cell wall galactan production through a sequence-specific polymerization.

  DOI：

  10.1021/ja301723p
• 作为产物：
  描述：

  2,3-di-O-benzyl-6-deoxy-6-iodo-α-D-methylgalactopyranose 在 正丁基锂 、 四丁基碘化铵 、 sodium hydroxide 、 碘甲烷 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 为溶剂， 以47%的产率得到2,3-di-O-benzyl-5-eno-β-D-methyl galactofuranose
  参考文献：
  名称：

  Fluorosugar Chain Termination Agents as Probes of the Sequence Specificity of a Carbohydrate Polymerase

  摘要：

  Naturally occurring carbohydrate polymers are ubiquitous. They are assembled by polymerizing glycosyltransferases, which can generate polysaccharide products with repeating sequence patterns. The fidelity of enzymes of this class is unknown. We report a method for testing the fidelity of carbohydrate polymerase pattern deposition: we synthesized fluorosugar donors and used them as chain termination agents. The requisite nucleotide fluorosugars could be produced from a single intermediate using the Jacobsen catalyst in a kinetically controlled separation of diastereomers. The resulting fluorosugar donors were used by the galactofuranosyltransferase GlfT2 from Mycobacterium tuberculosis, and the data indicate that this enzyme mediates the cell wall galactan production through a sequence-specific polymerization.

  DOI：

  10.1021/ja301723p