phenyl 2-O-benzoyl-1-thio-α-D-arabinofuranoside | 1207338-44-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 2-O-benzoyl-1-thio-α-D-arabinofuranoside
• 英文别名: [(2R,3S,4R,5R)-4-hydroxy-5-(hydroxymethyl)-2-phenylsulfanyloxolan-3-yl] benzoate
• CAS: 1207338-44-0
• 化学式: C₁₈H₁₈O₅S
• 分子量: 346.404
• InChiKey: IHUZQHUPJMLTJX-XLMAVXFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 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：

  phenyl 2-O-benzoyl-1-thio-α-D-arabinofuranoside 在 咪唑 、 N-碘代丁二酰亚胺 、 三氟甲磺酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 1-adamantyl 2-O-benzoyl-3,5-di-O-tert-butyldimethylsilyl-α-D-arabinofuranoside
  参考文献：
  名称：

  Tuning Effect of Silyl Protecting Groups on the Glycosylation Reactivity of Arabinofuranosyl Thioglycosides

  摘要：

  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.

  DOI：

  10.1021/ol401166x
• 作为产物：
  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

文献信息

• Regioselective Glycosylation Method Using Partially Protected Arabino- and Galactofuranosyl Thioglycosides as Key Glycosylating Substrates and Its Application to One-Pot Synthesis of Oligofuranoses
  作者：Li-Min Deng、Xia Liu、Xing-Yong Liang、Jin-Song Yang

  DOI：10.1021/jo300084g

  日期：2012.4.6

  development of a novel regioselective furanosylation methodology using partially protected furanosyl thioglycosides as central glycosylating building blocks and its application in the efficient one-pot synthesis of a series of linear and branched-type arabino- and galactofuranoside fragments structurally related to the cell wall polysaccharides of Mycobacterium tuberculosis, Streptococcus pneumoniae serostype

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