methyl 3-O-benzyl-5-O-p-methoxybenzyl-α-D-arabinofuranoside | 1236193-30-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-O-benzyl-5-O-p-methoxybenzyl-α-D-arabinofuranoside
• 英文别名: (2S,3S,4S,5R)-2-methoxy-5-[(4-methoxyphenyl)methoxymethyl]-4-phenylmethoxyoxolan-3-ol
• CAS: 1236193-30-8
• 化学式: C₂₁H₂₆O₆
• 分子量: 374.434
• InChiKey: NSSHUHULVSEEMH-MHTWAQMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 3-O-benzyl-5-O-p-methoxybenzyl-α-D-arabinofuranoside 、 Benzoic acid (2R,3R,4S,5R)-3,4-bis-benzyloxy-5-p-tolylsulfanyl-tetrahydro-furan-2-ylmethyl ester 在 N-碘代丁二酰亚胺 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以76%的产率得到methyl 5-O-benzoyl-2,3-di-O-benzyl-β-D-arabinofuranosyl-(1->2)-3-O-benzyl-5-O-p-methoxybenzyl-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：

  methyl 2,3-anhydro-5-O-p-methoxybenzyl-α-D-lyxofuranoside 、 苯甲醇钠 以 苯甲醇 为溶剂， 反应 24.0h， 以77%的产率得到methyl 3-O-benzyl-5-O-p-methoxybenzyl-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

文献信息

• 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.