3,5-di-O-benzoyl-α-D-ribofuranoside prop-2-ynyl-1,2-orthobenzoate | 66981-58-6

• 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-α-D-ribofuranoside prop-2-ynyl-1,2-orthobenzoate
• 英文别名: 3,5-di-O-benzoyl-α-D-ribofuranoside-prop-2-ynyl-1,2-orthobenzoate；3,5-Di-O-benzoyl-1,2-O-(1-propargyloxybenzyliden)-α-D-ribose；3,5-Di-O-benzoyl-1,2-O(1-propargyloxybenzyliden)-α-D-ribose
• CAS: 66981-58-6
• 化学式: C₂₉H₂₄O₈
• 分子量: 500.505
• InChiKey: CLQVTIBETVTHSK-CDIRFWPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.67
• 重原子数：
  37.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  89.52
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  3,5-di-O-benzoyl-α-D-ribofuranoside prop-2-ynyl-1,2-orthobenzoate 在 gold(III) chloride 、 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 6.0h， 生成 methyl 2,3,4-tri-O-benzyl-6-O-(2-O-benzoyl-3,5-di-O-benzyl-β-D-ribofuranosyl)-α-D-glucopyranoside
  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
• 作为产物：
  描述：

  卡培他滨杂质25 在 吡啶 、 2,6-二甲基吡啶 、 甲醇 、 乙酰溴 、 四丁基碘化铵 、 乙酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 3,5-di-O-benzoyl-α-D-ribofuranoside 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。
• 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.