(pent-4-enyl) 2,3,5-tri-O-benzoyl-α-D-arabinofuranoside | 1431370-38-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (pent-4-enyl) 2,3,5-tri-O-benzoyl-α-D-arabinofuranoside
• 英文别名: pent-4-enyl 2,3,5-tri-O-benzoyl-α-D-arabinofuranoside；n-pentenyl 2,3,5-tri-O-benzoyl-α-D-arabinofuranoside；[(2R,3R,4S,5S)-3,4-dibenzoyloxy-5-pent-4-enoxyoxolan-2-yl]methyl benzoate
• CAS: 1431370-38-5
• 化学式: C₃₁H₃₀O₈
• 分子量: 530.574
• InChiKey: FLWSIATXYDZOKY-BYBRNZAOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  39
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (pent-4-enyl) 2,3,5-tri-O-benzoyl-α-D-arabinofuranoside 在 溴 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 生成 2,3,5-tri-O-benzoyl-D-arabinofuranosyl bromide
  参考文献：
  名称：

  Efficient synthesis of oligosaccharyl 1,2-O-orthoesters from n-pentenyl glycosides and application to the pentaarabinofuranoside of the mycobacterial cell surface

  摘要：

  复杂的寡糖合成需要使用一个以上的糖基供体，因此，糖基供体之间的相互转化方法对整个合成计划非常重要。在这里，正戊烯基糖苷在酸和碱敏感官能团的存在下被有效地转化为糖基 1,2-O-正酯。发现所确定的方案也适用于合成三糖基和四糖基 1,2-O-缩酮。此外，该方法还完成了结核分枝杆菌细胞表面五碳呋喃糖苷的迭代合成。

  DOI：

  10.1039/c4ob01395f
• 作为产物：
  描述：

  methyl tri-O-benzoyl-α-D-arabinofuranoside 在 2,6-二甲基吡啶 、 甲醇 、 gold(III) chloride 、 乙酰溴 、 四丁基碘化铵 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 (pent-4-enyl) 2,3,5-tri-O-benzoyl-α-D-arabinofuranoside
  参考文献：
  名称：

  Facile Synthesis of β- and α-Arabinofuranosides and Application to Cell Wall Motifs of M. tuberculosis

  摘要：

  Propargyl 1,2-orthoesters of arabinose are exploited for the synthesis of 1,2-trans furanosides; easily accessible 1,2-trans ribofuranosides are converted to challenging 1,2-cis-arabinofuranosides by oxidoreduction. Utility of these protocols was demonstrated by the successful synthesis of major structural motifs present in the cell surface of Mycobacterium tuberculosis. Key furanosylations were carried out under gold-catalyzed glycosidation conditions.

  DOI：

  10.1021/ol400931p

文献信息

• Gold(III)-Catalyzed Glycosidations for 1,2-<i>trans</i> and 1,2-<i>cis</i> Furanosides
  作者：Shivaji A. Thadke、Bijoyananda Mishra、Srinivas Hotha

  DOI：10.1021/jo501052y

  日期：2014.8.15

  Stereoselective synthesis of furanosides is still a daunting task, unlike the pyranosides, for which several methods exist. Herein, a unified stereoselective strategy for the synthesis of 1,2-trans and 1,2-cis furanosides is revealed for seven out of eight possible isomers of pentoses. The identified protocol gives access to diastereoselective synthesis of α- and β-araf, ribf, lyxf, and α-xylf furanosides. 1,2-trans glycosides were synthesized by the use of propargyl 1,2-orthoesters under gold-catalyzed glycosidation conditions, and subsequently, they are converted into 1,2-cis glycosides through oxidation-reduction as the key functional group transformation. All the reactions are found to be fully diastereoselective, mild, and high yielding.
• Facile Synthesis of β- and α-Arabinofuranosides and Application to Cell Wall Motifs of <i>M. tuberculosis</i>
  作者：Shivaji A. Thadke、Bijoyananda Mishra、Srinivas Hotha

  DOI：10.1021/ol400931p

  日期：2013.5.17

  Propargyl 1,2-orthoesters of arabinose are exploited for the synthesis of 1,2-trans furanosides; easily accessible 1,2-trans ribofuranosides are converted to challenging 1,2-cis-arabinofuranosides by oxidoreduction. Utility of these protocols was demonstrated by the successful synthesis of major structural motifs present in the cell surface of Mycobacterium tuberculosis. Key furanosylations were carried out under gold-catalyzed glycosidation conditions.
• Efficient synthesis of oligosaccharyl 1,2-O-orthoesters from n-pentenyl glycosides and application to the pentaarabinofuranoside of the mycobacterial cell surface
  作者：Shivaji A. Thadke、Srinivas Hotha

  DOI：10.1039/c4ob01395f

  日期：——

  Complex oligosaccharide syntheses employ the use of more than one glycosyl donor and hence, methods for the interconversion of glycosyl donors are highly valuable for the overall synthesis plan. Herein, n-pentenyl glycosides are efficiently converted to glycosyl 1,2-O-orthoesters in the presence of both acid and base sensitive functional groups. The identified protocol was found to be suitable for the synthesis of trisaccharyl and tetrasaccharyl 1,2-O-orthoester as well. Furthermore, an iterative synthesis of pentaarabinofuranoside present on the Mycobacterium tuberculosis cell surface was accomplished using this method.

  复杂的寡糖合成需要使用一个以上的糖基供体，因此，糖基供体之间的相互转化方法对整个合成计划非常重要。在这里，正戊烯基糖苷在酸和碱敏感官能团的存在下被有效地转化为糖基 1,2-O-正酯。发现所确定的方案也适用于合成三糖基和四糖基 1,2-O-缩酮。此外，该方法还完成了结核分枝杆菌细胞表面五碳呋喃糖苷的迭代合成。