p-tolyl 2,3,5-tri-O-acetyl-1-thio-β-D-xylofuranoside | 828930-34-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-tolyl 2,3,5-tri-O-acetyl-1-thio-β-D-xylofuranoside
• CAS: 828930-34-3
• 化学式: C₁₈H₂₂O₇S
• 分子量: 382.434
• InChiKey: ZGLXRGOLHXAWPQ-XDNAFOTISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.24
• 重原子数：
  26.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  88.13
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  p-tolyl 2,3,5-tri-O-acetyl-1-thio-β-D-xylofuranoside 在 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 以92%的产率得到p-tolyl 1-thio-β-D-xylofuranoside
  参考文献：
  名称：

  An efficient route to thioglycosides with the 2,3-anhydro-d-ribo stereochemistry

  摘要：

  An improved route for the synthesis of p-tolyl 2,3-anhydro- 5-O-benzoyl-1-thio-beta-D-ribofurano side and its alpha anomer, which are important intermediates in the synthesis of (alpha- and beta- D-arabinofuranosides, has been developed. The products are obtained in six steps from D-xylose in 39% overall yield. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.10.009
• 作为产物：
  描述：

  4-甲苯硫酚 、 1,2,3,5-四乙酰基-D－木呋喃糖 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以74%的产率得到p-tolyl 2,3,5-tri-O-acetyl-1-thio-β-D-xylofuranoside
  参考文献：
  名称：

  An efficient route to thioglycosides with the 2,3-anhydro-d-ribo stereochemistry

  摘要：

  An improved route for the synthesis of p-tolyl 2,3-anhydro- 5-O-benzoyl-1-thio-beta-D-ribofurano side and its alpha anomer, which are important intermediates in the synthesis of (alpha- and beta- D-arabinofuranosides, has been developed. The products are obtained in six steps from D-xylose in 39% overall yield. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.10.009

文献信息

• Transition-metal-free synthesis of aryl 1-thioglycosides with arynes at room temperature
  作者：Yao Liu、Xiao-Bing Yu、Xiang-Mei Zhang、Qian Zhong、Li-Hua Liao、Nan Yan

  DOI：10.1039/d1ra04013h

  日期：——

  transition-metal-free protocol for the synthesis of aryl 1-thioglycosides is presented via arynes generated in situ combined with glycosyl thiols in the presence of TBAF(tBuOH)4. The methodology provides a general and efficient way to prepare a series of functionalized thioglycosides in good to excellent yields with a perfect control of the anomeric configuration at room temperature. In addition, the reaction

  在 TBAF( t BuOH) 4存在下，通过原位生成的芳烃与糖基硫醇结合，提出了一种温和、方便且不含过渡金属的芳基 1-硫糖苷合成方案。该方法提供了一种通用且有效的方法来制备一系列功能化的硫糖苷，并在室温下完美控制异头构型。此外，反应条件耐受多种戊糖和己糖，反应在受保护的单糖和二糖上也能顺利进行。