3,5-di-O-benzoyl-β-D-arabinofuranoside prop-2-ynyl-1,2-orthobenzoate | 1431370-34-1

• 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: 3,5-di-O-benzoyl-β-D-arabinofuranoside prop-2-ynyl-1,2-orthobenzoate
• 英文别名: [(3aS,5R,6R,6aS)-6-benzoyloxy-2-phenyl-2-prop-2-ynoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methyl benzoate
• CAS: 1431370-34-1
• 化学式: C₂₉H₂₄O₈
• 分子量: 500.505
• InChiKey: CLQVTIBETVTHSK-SKKUQAGNSA-N

物化性质

• 沸点：
  639.7±55.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  37
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  89.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3,5-di-O-benzoyl-β-D-arabinofuranoside prop-2-ynyl-1,2-orthobenzoate 在 sodium methylate 、 sodium hydride 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 4.0h， 生成 3,5-di-O-benzyl-β-D-arabinofuranoside (prop-2-yn-1-yl)-1,2-orthobenzoate
  参考文献：
  名称：

  Gold(III)-Catalyzed Glycosidations for 1,2-trans and 1,2-cis Furanosides

  摘要：

  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.

  DOI：

  10.1021/jo501052y
• 作为产物：
  描述：

  methyl tri-O-benzoyl-α-D-arabinofuranoside 在 2,6-二甲基吡啶 、 甲醇 、 乙酰溴 、 四丁基碘化铵 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 3,5-di-O-benzoyl-β-D-arabinofuranoside prop-2-ynyl-1,2-orthobenzoate
  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

• Facile synthesis of aminooxy glycosides by gold(III)-catalyzed glycosidation
  作者：Shivaji A. Thadke、Mahesh Neralkar、Srinivas Hotha

  DOI：10.1016/j.carres.2016.04.022

  日期：2016.7

  including glucosyl, mannosyl, galactosyl, ribofuranosyl, arabinofuranosyl, lyxofuranosyl and xylofuranosyl using gold catalysis repertoire. The protocol is identified to be compatible for the synthesis of aminooxy glycosides of higher oligosaccharides as well.

  据报道，在金（III）催化的糖苷化条件下，用各种醛糖衍生的炔丙基1,2-原酸酯对羟基琥珀酰亚胺和羟基邻苯二甲酰亚胺进行了O-糖基化。使用金催化库，由相应的糖基原酸酯，包括葡萄糖基，甘露糖基，半乳糖基，核呋喃糖基，阿拉伯呋喃糖基，莱呋喃呋喃糖基和木呋喃糖基，合成了多种羟基琥珀酰亚胺基和羟基邻苯二甲酰亚胺基糖苷。该方案经鉴定也可用于高级寡糖的氨基氧基糖苷的合成。
• Stable Alkynyl Glycosyl Carbonates: Catalytic Anomeric Activation and Synthesis of a Tridecasaccharide Reminiscent of<i>Mycobacterium tuberculosis</i>Cell Wall Lipoarabinomannan
  作者：Bijoyananda Mishra、Mahesh Neralkar、Srinivas Hotha

  DOI：10.1002/anie.201511695

  日期：2016.6.27

  a challenging task despite the advent of modern glycosidation techniques. Herein, alkynyl glycosyl carbonates are shown to be stable glycosyl donors that can be activated catalytically by gold and silver salts at 25 °C in just 15 min to produce glycosides in excellent yields. Benzoyl glycosyl carbonate donors are solid compounds with a long shelf life. This operationally simple protocol was found to

  尽管现代糖苷化技术的出现，寡糖的合成仍然是一项艰巨的任务。本文中，炔基糖基碳酸酯显示为稳定的糖基供体，其可在25℃下仅15分钟内被金和银盐催化活化，从而以优异的产率产生糖苷。苯甲酰基糖基碳酸酯供体是具有长保存期限的固体化合物。发现该操作简单的方案对于核苷，氨基酸以及酚和叠氮基糖缀合物的合成是高效的。碳酸盐糖苷化方法的重复使用使得十三碳阿拉伯甘露聚糖能够以快速的方式高度收敛地合成。
• 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。
• A Versatile Synthesis of Pentacosafuranoside Subunit Reminiscent of Mycobacterial Arabinogalactan Employing One Strategic Glycosidation Protocol
  作者：Sandip Pasari、Sujit Manmode、Gulab Walke、Srinivas Hotha

  DOI：10.1002/chem.201704009

  日期：2018.1.24

  reactions. Several linear and branched oligosaccharides were synthesised ranging from trisaccharide to pentadecasaccharide during this endeavour. Synthesis of pentacosasaccharide was accomplished in 77 steps with 0.0012 % overall yield. These oligosaccharides are envisioned to be excellent probes for understanding disease biology thereby facilitating discovery of novel antitubercular agents, vaccines and/or

  寡糖涉及多种生物学现象。如果可以获取均质且定义明确的寡糖，则可以进行许多糖生物学实验。分枝杆菌细胞壁含有阿拉伯半乳聚糖作为挑战化学合成的主要成分之一。因此，该研究的主要目的是合成阿拉伯半乳聚糖的主要寡糖部分。五聚呋喃糖苷（25mer）的合成涉及通过邻基团的1,2-反式连接和1,2-顺式Araf的氧化还原策略来安装数个阿拉伯呋喃糖基连接。甲策略性地放置Ñ还原端的戊烯基部分使生物分子探针能够通过著名的交叉易位或硫醇-烯点击反应进行连接。在此过程中，合成了几种直链和支链寡糖，范围从三糖到十五糖。五糖的合成以77个步骤完成，总产率为0.0012％。这些低聚糖被认为是了解疾病生物学的极佳探针，从而有助于发现新型抗结核药，疫苗和/或诊断方法。