phenyl 5-O-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)-2,3-di-O-benzoyl-1-thio-α-D-arabinofuranoside | 1207338-47-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: phenyl 5-O-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)-2,3-di-O-benzoyl-1-thio-α-D-arabinofuranoside
• 英文别名: Bz(-2)[Bz(-3)][Bz(-5)]D-Araf(a1-5)[Bz(-2)][Bz(-3)]D-Araf(a)-SPh；[(2R,3R,4S,5S)-3,4-dibenzoyloxy-5-[[(2R,3R,4S,5R)-3,4-dibenzoyloxy-5-phenylsulfanyloxolan-2-yl]methoxy]oxolan-2-yl]methyl benzoate
• CAS: 1207338-47-3
• 化学式: C₅₁H₄₂O₁₃S
• 分子量: 894.953
• InChiKey: IDJIMUHXZJDOOX-IHTGRHJCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10
• 重原子数：
  65
• 可旋转键数：
  21
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  185
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  phenyl 5-O-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)-2,3-di-O-benzoyl-1-thio-α-D-arabinofuranoside 、 methyl 2,3-di-O-benzoyl-α-D-arabinofuranoside 在 N-碘代丁二酰亚胺 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以48 mg的产率得到methyl 5-O-[5-O-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)-2,3-di-O-benzoyl-α-D-arabinofuranosyl]-2,3-di-O-benzoyl-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
• 作为产物：
  描述：

  phenyl 2,3-di-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94%的产率得到phenyl 5-O-(2,3,5-tri-O-benzoyl-α-D-arabinofuranosyl)-2,3-di-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.