p-methylphenyl 2-O-benzoyl-1-thio-α-D-arabinofuranoside | 1207338-45-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-methylphenyl 2-O-benzoyl-1-thio-α-D-arabinofuranoside
• 英文别名: [(2R,3S,4R,5R)-4-hydroxy-5-(hydroxymethyl)-2-(4-methylphenyl)sulfanyloxolan-3-yl] benzoate
• CAS: 1207338-45-1
• 化学式: C₁₉H₂₀O₅S
• 分子量: 360.431
• InChiKey: CHRUKPMSVPSVGM-VXIBKDFQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  p-methylphenyl 2-O-benzoyl-1-thio-α-D-arabinofuranoside 、 2,3,5-tri-O-benzoyl-D-arabinofuranosyl trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 以91%的产率得到Α-D-ARABINOFURANOSIDE,4-METHYLPHENYL1-THIO-,2,3,5-TRIBENZOATEΑ-D-阿拉伯呋喃糖苷,4-甲基苯基1-硫代2,3,5-苯三甲酸酯
  参考文献：
  名称：

  Efficient one-pot syntheses of α-d-arabinofuranosyl tri- and tetrasaccharides present in cell wall polysaccharide of Mycobacterium tuberculosis

  摘要：

  Two alpha-D-arabinofuramosyl oligosaccharides (2 and 3) found as constituent parts of the polysaccharide portion from the cell wall of Mycobacterium tuberculosis have been efficiently synthesized via a one-pot glycosylation procedure in which a key step is the chemoselective activation between D-arabinofuranosyl trichloroacetimidate donor 4 and partially protected aryl thioglycosides 5 or 7, respectively. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.11.038
• 作为产物：
  描述：

  在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以70%的产率得到p-methylphenyl 2-O-benzoyl-1-thio-α-D-arabinofuranoside
  参考文献：
  名称：

  Efficient one-pot syntheses of α-d-arabinofuranosyl tri- and tetrasaccharides present in cell wall polysaccharide of Mycobacterium tuberculosis

  摘要：

  Two alpha-D-arabinofuramosyl oligosaccharides (2 and 3) found as constituent parts of the polysaccharide portion from the cell wall of Mycobacterium tuberculosis have been efficiently synthesized via a one-pot glycosylation procedure in which a key step is the chemoselective activation between D-arabinofuranosyl trichloroacetimidate donor 4 and partially protected aryl thioglycosides 5 or 7, respectively. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.11.038

文献信息

• Efficient one-pot syntheses of α-d-arabinofuranosyl tri- and tetrasaccharides present in cell wall polysaccharide of Mycobacterium tuberculosis
  作者：Xing-Yong Liang、Li-Min Deng、Xia Liu、Jin-Song Yang

  DOI：10.1016/j.tet.2009.11.038

  日期：2010.1

  Two alpha-D-arabinofuramosyl oligosaccharides (2 and 3) found as constituent parts of the polysaccharide portion from the cell wall of Mycobacterium tuberculosis have been efficiently synthesized via a one-pot glycosylation procedure in which a key step is the chemoselective activation between D-arabinofuranosyl trichloroacetimidate donor 4 and partially protected aryl thioglycosides 5 or 7, respectively. (C) 2009 Elsevier Ltd. All rights reserved.