methyl 5-O-{3,5-di-O-(2-O-[2,3,5-tri-O-benzyl-β-D-arabinofuranosyl]-3,5-di-O-benzyl-α-D-arabinofuranosyl)-2-O-benzoyl-α-arabinofuranosyl}-2,3-di-O-benzoyl-α-D-arabinofuranoside | 278796-54-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 5-O-{3,5-di-O-(2-O-[2,3,5-tri-O-benzyl-β-D-arabinofuranosyl]-3,5-di-O-benzyl-α-D-arabinofuranosyl)-2-O-benzoyl-α-arabinofuranosyl}-2,3-di-O-benzoyl-α-D-arabinofuranoside
• 英文别名: methyl 5-O-{3,5-di-O-(2-O-[2,3,5-tri-O-benzyl-β-D-arabinofuranosyl]-3,5-di-O-benzyl-α-D-arabinofuranosyl)-2-O-benzoyl-α-D-arabinofuranosyl}-2,3-di-O-benzoyl-α-D-arabinofuranoside；Bn(-2)[Bn(-3)][Bn(-5)]D-Araf(b1-2)[Bn(-3)][Bn(-5)]D-Araf(a1-3)[Bn(-2)[Bn(-3)][Bn(-5)]D-Araf(b1-2)[Bn(-3)][Bn(-5)]D-Araf(a1-5)][Bz(-2)]D-Araf(a1-5)[Bz(-2)][Bz(-3)]a-D-Araf1Me；[(2R,3R,4S,5S)-4-benzoyloxy-2-[[(2S,3S,4R,5R)-3-benzoyloxy-4-[(2S,3S,4R,5R)-3-[(2S,3S,4R,5R)-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)oxolan-2-yl]oxy-4-phenylmethoxy-5-(phenylmethoxymethyl)oxolan-2-yl]oxy-5-[[(2S,3S,4R,5R)-3-[(2S,3S,4R,5R)-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)oxolan-2-yl]oxy-4-phenylmethoxy-5-(phenylmethoxymethyl)oxolan-2-yl]oxymethyl]oxolan-2-yl]oxymethyl]-5-methoxyoxolan-3-yl] benzoate
• CAS: 278796-54-6
• 化学式: C₁₂₂H₁₂₄O₂₈
• 分子量: 2038.31
• InChiKey: UJUMLLVPRUQMGN-IANHHSMYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  17.4
• 重原子数：
  150
• 可旋转键数：
  56
• 环数：
  19.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  282
• 氢给体数：
  0
• 氢受体数：
  28

反应信息

• 作为反应物：
  描述：

  methyl 5-O-{3,5-di-O-(2-O-[2,3,5-tri-O-benzyl-β-D-arabinofuranosyl]-3,5-di-O-benzyl-α-D-arabinofuranosyl)-2-O-benzoyl-α-arabinofuranosyl}-2,3-di-O-benzoyl-α-D-arabinofuranoside 在 palladium on activated charcoal sodium methylate 、 氢气 作用下， 以 甲醇 、 二氯甲烷 、 水 、 溶剂黄146 为溶剂， 反应 7.0h， 以86%的产率得到methyl 5-O-{3,5-di-O-(2-O-[β-D-arabinofuranosyl]-α-D-arabinofuranosyl)-α-D-arabinofuranosyl}-α-D-arabinofuranoside
  参考文献：
  名称：

  The First Total Synthesis of a Highly Branched Arabinofuranosyl Hexasaccharide Found at the Nonreducing Termini of Mycobacterial Arabinogalactan and Lipoarabinomannan

  摘要：

  [GRAPHICS]The first total synthesis of the arabinofuranosyl hexasaccharide present at the nonreducing termini of mycobacterial arabinogalactan and lipoarabinomannan is reported. The oligosaccharide was prepared as its methyl glycoside via a route that is both highly efficient and convergent. Addition of two beta-D arabinofuranosyl residues simultaneously in high yield and with excellent stereocontrol was the key step of the synthesis.

  DOI：

  10.1021/ol005907g
• 作为产物：
  描述：

  methyl 5-O-[3,5-di-O-(3,5-di-O-benzyl-α-D-arabinofuranosyl)-2-O-benzyl-α-D-arabinofuranosyl]-2,3-di-O-benzyl-α-D-arabinofuranoside 、 p-cresyl 2,3,5-tri-O-benzyl-1-thio-D-arabinofuranoside 在 N-碘代丁二酰亚胺 、 molecular sieve 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以81%的产率得到methyl 5-O-{3,5-di-O-(2-O-[2,3,5-tri-O-benzyl-β-D-arabinofuranosyl]-3,5-di-O-benzyl-α-D-arabinofuranosyl)-2-O-benzoyl-α-arabinofuranosyl}-2,3-di-O-benzoyl-α-D-arabinofuranoside
  参考文献：
  名称：

  分枝杆菌的阿拉伯呋喃糖苷：高度分支的六糖及其相关片段的合成，其中包含β-阿拉伯呋喃糖基残基。

  摘要：

  报道了11种含有β-阿拉伯呋喃糖基残基的寡糖（4-14）的合成。聚糖是分枝杆菌细胞壁复合物中发现的两种多糖阿拉伯半乳聚糖和脂质阿拉伯糖甘露聚糖的全部片段。在制备靶标中，关键步骤是低温糖基化反应，该反应安装了具有良好至优异立体控制效果的β-阿拉伯呋喃糖基残基。

  DOI：

  10.1021/jo010910e

文献信息

• Arabinofuranosides from Mycobacteria:  Synthesis of a Highly Branched Hexasaccharide and Related Fragments Containing β-Arabinofuranosyl Residues
  作者：Haifeng Yin、Francis W. D'Souz、Todd L. Lowary

  DOI：10.1021/jo010910e

  日期：2002.2.1

  The synthesis of 11 oligosaccharides (4-14) containing beta-arabinofuranosyl residues is reported. The glycans are all fragments of two polysaccharides, arabinogalactan and lipoarabinomannan, which are found in the cell wall complex of mycobacteria. In the preparation of the targets, the key step was a low-temperature glycosylation reaction that installed the beta-arabinofuranosyl residues with good

  报道了11种含有β-阿拉伯呋喃糖基残基的寡糖（4-14）的合成。聚糖是分枝杆菌细胞壁复合物中发现的两种多糖阿拉伯半乳聚糖和脂质阿拉伯糖甘露聚糖的全部片段。在制备靶标中，关键步骤是低温糖基化反应，该反应安装了具有良好至优异立体控制效果的β-阿拉伯呋喃糖基残基。
• The First Total Synthesis of a Highly Branched Arabinofuranosyl Hexasaccharide Found at the Nonreducing Termini of Mycobacterial Arabinogalactan and Lipoarabinomannan
  作者：Francis W. D'Souz、Todd L. Lowary

  DOI：10.1021/ol005907g

  日期：2000.5.1

  [GRAPHICS]The first total synthesis of the arabinofuranosyl hexasaccharide present at the nonreducing termini of mycobacterial arabinogalactan and lipoarabinomannan is reported. The oligosaccharide was prepared as its methyl glycoside via a route that is both highly efficient and convergent. Addition of two beta-D arabinofuranosyl residues simultaneously in high yield and with excellent stereocontrol was the key step of the synthesis.