2-(5-O-benzoyl-2-deoxy-2-(p-thiotolyl)-β-D-xylofuranosyl)acetophenone | 1185748-18-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(5-O-benzoyl-2-deoxy-2-(p-thiotolyl)-β-D-xylofuranosyl)acetophenone
• 英文别名: [(2R,3S,4R,5S)-3-hydroxy-4-(4-methylphenyl)sulfanyl-5-phenacyloxolan-2-yl]methyl benzoate
• CAS: 1185748-18-8
• 化学式: C₂₇H₂₆O₅S
• 分子量: 462.566
• InChiKey: DYGQAEPRXRFGDL-QYOOZWMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  98.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(5-O-benzoyl-2-deoxy-2-(p-thiotolyl)-β-D-xylofuranosyl)acetophenone 在 sodium tetrahydroborate 、 sodium methylate 、 戴斯-马丁氧化剂 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 8.5h， 生成 2-(3,5-O-isopropylidene-2-deoxy-2-(p-thiocresyl)-β-D-xylofuranosyl)acetophenone
  参考文献：
  名称：

  2,3-Anhydrosugars in glycoside bond synthesis: application to furanosyl azides and C-glycosides

  摘要：

  The preparation of 2-deoxy-2-thiotolylfuranosyl azides and C-glycosides from a 2,3-anhydrosugar thioglycoside with the D-lyxo stereochemistry is described. The reaction is performed by treatment of the thioglycoside with a trimethylsilylated nucleophile in the presence of BF3 center dot OEt2. This approach provides a convenient route to the preparation of the corresponding 2-deoxy-furanosyl azides and C-glycosides. In contrast, the use of an isomeric substrate, with the 2,3-anhydro-D-ribo stereochemistry, gave these products in low to modest yield. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.06.008
• 作为产物：
  描述：

  1-苯基-1-三甲基硅氧乙烯 、 p-tolyl 2,3-anhydro-5-O-benzoyl-1-thio-α-D-lyxofuranoside 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以82%的产率得到2-(5-O-benzoyl-2-deoxy-2-(p-thiotolyl)-β-D-xylofuranosyl)acetophenone
  参考文献：
  名称：

  2,3-Anhydrosugars in glycoside bond synthesis: application to furanosyl azides and C-glycosides

  摘要：

  The preparation of 2-deoxy-2-thiotolylfuranosyl azides and C-glycosides from a 2,3-anhydrosugar thioglycoside with the D-lyxo stereochemistry is described. The reaction is performed by treatment of the thioglycoside with a trimethylsilylated nucleophile in the presence of BF3 center dot OEt2. This approach provides a convenient route to the preparation of the corresponding 2-deoxy-furanosyl azides and C-glycosides. In contrast, the use of an isomeric substrate, with the 2,3-anhydro-D-ribo stereochemistry, gave these products in low to modest yield. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.06.008

文献信息

• 2,3-Anhydrosugars in glycoside bond synthesis: application to furanosyl azides and C-glycosides
  作者：Dianjie Hou、Todd L. Lowary

  DOI：10.1016/j.tet.2009.06.008

  日期：2009.8

  The preparation of 2-deoxy-2-thiotolylfuranosyl azides and C-glycosides from a 2,3-anhydrosugar thioglycoside with the D-lyxo stereochemistry is described. The reaction is performed by treatment of the thioglycoside with a trimethylsilylated nucleophile in the presence of BF3 center dot OEt2. This approach provides a convenient route to the preparation of the corresponding 2-deoxy-furanosyl azides and C-glycosides. In contrast, the use of an isomeric substrate, with the 2,3-anhydro-D-ribo stereochemistry, gave these products in low to modest yield. (C) 2009 Elsevier Ltd. All rights reserved.