3-(5-O-benzoyl-2-deoxy-2-(p-thiotolyl)-β-D-xylofuranosyl)-1-propene | 1185748-17-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(5-O-benzoyl-2-deoxy-2-(p-thiotolyl)-β-D-xylofuranosyl)-1-propene
• 英文别名: [(2R,3S,4R,5S)-3-hydroxy-4-(4-methylphenyl)sulfanyl-5-prop-2-enyloxolan-2-yl]methyl benzoate
• CAS: 1185748-17-7
• 化学式: C₂₂H₂₄O₄S
• 分子量: 384.496
• InChiKey: VIJJBAASPQDZJM-WOZUAGRISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  81.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(5-O-benzoyl-2-deoxy-2-(p-thiotolyl)-β-D-xylofuranosyl)-1-propene 在 sodium methylate 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 4.0h， 生成 1-(3,5-O-isopropylidene-2-deoxy-2-(p-thiocresyl)-α-D-xylofuranosyl)-3-propene
  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：

  p-tolyl 2,3-anhydro-5-O-benzoyl-1-thio-α-D-lyxofuranoside 、 烯丙基三甲基硅烷 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以86%的产率得到3-(5-O-benzoyl-2-deoxy-2-(p-thiotolyl)-β-D-xylofuranosyl)-1-propene
  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.