phenyl 2-O-benzoyl-3,5-O-(di-tert-butylsilylene)-1-thio-α-D-arabinofuranoside | 1207338-43-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: phenyl 2-O-benzoyl-3,5-O-(di-tert-butylsilylene)-1-thio-α-D-arabinofuranoside
• CAS: 1207338-43-9
• 化学式: C₂₆H₃₄O₅SSi
• 分子量: 486.704
• InChiKey: QDTRASDTGBIRLS-PIATZUFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.19
• 重原子数：
  33.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  phenyl 2-O-benzoyl-3,5-O-(di-tert-butylsilylene)-1-thio-α-D-arabinofuranoside 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以72%的产率得到phenyl 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
• 作为产物：
  描述：

  phenyl 3,5-O-(di-tert-butylsilanediyl)-1-thio-α-D-arabinofuranoside 、 苯甲酰氯 在 吡啶 作用下， 以93%的产率得到phenyl 2-O-benzoyl-3,5-O-(di-tert-butylsilylene)-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

• Tuning Effect of Silyl Protecting Groups on the Glycosylation Reactivity of Arabinofuranosyl Thioglycosides
  作者：Xing-Yong Liang、Hua-Chao Bin、Jin-Song Yang

  DOI：10.1021/ol401166x

  日期：2013.6.7

  The tuning effect of silyl protecting groups on the glycosylation reactivity of arabinofuranosyl phenyl thioglycoside donors Is presented. Silyl ethers on the 3-, 5-, and 3,5-positions of the arabinofuranose ring are found to have an arming effect on the donor reactivity, whereas the cyclic 3,5-acetal type protecting groups reduce the reactivity.