methyl 2,3-di-O-benzyl-α-D-arabinofuranosyl-(1->3)-[2,3-di-O-benzyl-α-D-arabinofuranosyl-(1->5)]-2-O-benzyl-α-D-arabino-furanoside | 1236193-44-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3-di-O-benzyl-α-D-arabinofuranosyl-(1->3)-[2,3-di-O-benzyl-α-D-arabinofuranosyl-(1->5)]-2-O-benzyl-α-D-arabino-furanoside
• 英文别名: Bn(-2)[Bn(-3)]D-Araf(a1-3)[Bn(-2)[Bn(-3)]D-Araf(a1-5)][Bn(-2)]a-D-Araf1Me；[(2R,3R,4S,5S)-5-[[(2R,3R,4S,5S)-3-[(2R,3S,4R,5R)-5-(hydroxymethyl)-3,4-bis(phenylmethoxy)oxolan-2-yl]oxy-5-methoxy-4-phenylmethoxyoxolan-2-yl]methoxy]-3,4-bis(phenylmethoxy)oxolan-2-yl]methanol
• CAS: 1236193-44-4
• 化学式: C₅₁H₅₈O₁₃
• 分子量: 879.014
• InChiKey: RHLSOLZMXTTWOY-PTNJNLODSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  64
• 可旋转键数：
  23
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  142
• 氢给体数：
  2
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  methyl 2,3-di-O-benzyl-α-D-arabinofuranosyl-(1->3)-[2,3-di-O-benzyl-α-D-arabinofuranosyl-(1->5)]-2-O-benzyl-α-D-arabino-furanoside 、 棕榈酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以89%的产率得到methyl 2,3-di-O-benzyl-5-O-palmitoyl-α-D-arabinofuranosyl-(1->3)-[2,3-di-O-benzyl-5-O-palmitoyl-α-D-arabinofuranosyl-(1->5)]-2-O-benzyl-α-D-arabinofuranoside
  参考文献：
  名称：

  Probing the Effect of Acylation on Arabinofuranose Ring Conformation in Di- and Trisaccharide Fragments of Mycobacterial Arabinogalactan

  摘要：

  A major component of the cell wall of mycobacteria is the mycolyl-arabinogalactan (mAG) complex. The arabinose and galactose residues in mAG are found solely in the furanose form, and it has been suggested that the flexibility of these five-membered rings allows for the tight packing of mycolic acids. In order to probe the "flexible scaffold hypothesis", we designed and synthesized glycolipids 3-6 and 8-11 as simple models of the terminal portion of mAG. A set of donors and acceptors were explored for preparing the key beta-(1 -> 2) linkage in 2-6, and the best selectivity and yield can be obtained by using the electron-rich thioglycoside donor 14 and the O-5 p-methoxybenzyl-protected acceptor 17. Both alpha-linkages in the trisaccharides 7-11 were formed in a one-pot reaction. The conformations of compounds 2-11 were studied using solution-state NMR spectroscopy, but little change was observed in the coupling constants for the ring protons between 2 and 3-6 or between 7 and 8-11. However, the rotamer populations about the C-4-C-5 bond for the beta-linked ring in disaccharide 2 did change upon acylation at O-5.

  DOI：

  10.1021/jo100575a
• 作为产物：
  描述：

  在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以77%的产率得到methyl 2,3-di-O-benzyl-α-D-arabinofuranosyl-(1->3)-[2,3-di-O-benzyl-α-D-arabinofuranosyl-(1->5)]-2-O-benzyl-α-D-arabino-furanoside
  参考文献：
  名称：

  由确定的合成霉菌酸制备分枝杆菌阿拉伯半乳聚糖的三阿拉伯糖基二霉酸酯片段。

  摘要：

  描述了一种有效的合成方法，使用结构上定义的合成α-，酮和甲氧基霉菌酸合成三阿拉伯糖基二霉菌酸酯。

  DOI：

  10.1016/j.carres.2016.11.006

文献信息

• Preparation of the tri-arabino di-mycolate fragment of mycobacterial arabinogalactan from defined synthetic mycolic acids
  作者：Mohsin O. Mohammed、Juma'a R. Al Dulayymi、Mark S. Baird

  DOI：10.1016/j.carres.2016.11.006

  日期：2017.1

  An efficient synthetic approach to tri-arabino di-mycolates, using structurally defined synthetic alpha-, keto and methoxy mycolic acids is described.

  描述了一种有效的合成方法，使用结构上定义的合成α-，酮和甲氧基霉菌酸合成三阿拉伯糖基二霉菌酸酯。
• Probing the Effect of Acylation on Arabinofuranose Ring Conformation in Di- and Trisaccharide Fragments of Mycobacterial Arabinogalactan
  作者：Chunjuan Liu、Michele R. Richards、Todd L. Lowary

  DOI：10.1021/jo100575a

  日期：2010.8.6

  A major component of the cell wall of mycobacteria is the mycolyl-arabinogalactan (mAG) complex. The arabinose and galactose residues in mAG are found solely in the furanose form, and it has been suggested that the flexibility of these five-membered rings allows for the tight packing of mycolic acids. In order to probe the "flexible scaffold hypothesis", we designed and synthesized glycolipids 3-6 and 8-11 as simple models of the terminal portion of mAG. A set of donors and acceptors were explored for preparing the key beta-(1 -> 2) linkage in 2-6, and the best selectivity and yield can be obtained by using the electron-rich thioglycoside donor 14 and the O-5 p-methoxybenzyl-protected acceptor 17. Both alpha-linkages in the trisaccharides 7-11 were formed in a one-pot reaction. The conformations of compounds 2-11 were studied using solution-state NMR spectroscopy, but little change was observed in the coupling constants for the ring protons between 2 and 3-6 or between 7 and 8-11. However, the rotamer populations about the C-4-C-5 bond for the beta-linked ring in disaccharide 2 did change upon acylation at O-5.