ethyl 5-O-(β-D-galactofuranosyl)-2,3,6-tri-O-benzyl-β-D-galactofuranoside | 352463-50-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 5-O-(β-D-galactofuranosyl)-2,3,6-tri-O-benzyl-β-D-galactofuranoside
• 英文别名: Galf(b1-5)[Bn(-2)][Bn(-3)][Bn(-6)]Galf(b)-O-Et；(2S,3R,4R,5R)-2-[(1R)-1,2-dihydroxyethyl]-5-[(1R)-1-[(2S,3S,4R,5R)-5-ethoxy-3,4-bis(phenylmethoxy)oxolan-2-yl]-2-phenylmethoxyethoxy]oxolane-3,4-diol
• CAS: 352463-50-4
• 化学式: C₃₅H₄₄O₁₁
• 分子量: 640.728
• InChiKey: FHZCAGOPVZFQAB-PROCLVDHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  46
• 可旋转键数：
  17
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  146
• 氢给体数：
  4
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  ethyl 5-O-(β-D-galactofuranosyl)-2,3,6-tri-O-benzyl-β-D-galactofuranoside 在 palladium dihydroxide 氢气 作用下， 以 甲醇 为溶剂， 反应 8.0h， 以88%的产率得到ethyl 5-O-(β-D-galactofuranosyl)-β-D-galactofuranoside
  参考文献：
  名称：

  Synthesis of Oligosaccharides of Motifs D and E of Arabinogalactan Present in Mycobacterium tuberculosis

  摘要：

  Syntheses of the ethyl glycosides of 5-O-(beta -D-galactofuranosyl)-beta -D-galactofuranose and 5-O-(alpha -D-arabinofuranosyl)-6-O-(beta -D-galactofuranosyl)-beta -D-galactofuranose present in motifs D and E of Mycobacterium tuberculosis arabinogalactan, respectively, have been presented. The pentenyl-mediated O-glycosylation reaction was utilized to obtain the disaccharide of motif D. The first coupling reaction to prepare the inner disaccharide portion of motif E was accomplished by trichloroacetamidate method while the installation of the terminal sugar by pentenyl glycosylation approach was successful.

  DOI：

  10.1021/jo010180a
• 作为产物：
  描述：

  1,2,3,5,6-penta-O-acetyl-β-D-galactofuranose 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 4 A molecular sieve 、 三氟化硼乙醚 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 28.0h， 生成 ethyl 5-O-(β-D-galactofuranosyl)-2,3,6-tri-O-benzyl-β-D-galactofuranoside
  参考文献：
  名称：

  Synthesis of Oligosaccharides of Motifs D and E of Arabinogalactan Present in Mycobacterium tuberculosis

  摘要：

  Syntheses of the ethyl glycosides of 5-O-(beta -D-galactofuranosyl)-beta -D-galactofuranose and 5-O-(alpha -D-arabinofuranosyl)-6-O-(beta -D-galactofuranosyl)-beta -D-galactofuranose present in motifs D and E of Mycobacterium tuberculosis arabinogalactan, respectively, have been presented. The pentenyl-mediated O-glycosylation reaction was utilized to obtain the disaccharide of motif D. The first coupling reaction to prepare the inner disaccharide portion of motif E was accomplished by trichloroacetamidate method while the installation of the terminal sugar by pentenyl glycosylation approach was successful.

  DOI：

  10.1021/jo010180a

文献信息

• Synthesis of Oligosaccharides of Motifs D and E of Arabinogalactan Present in <i>Mycobacterium </i><i>t</i><i>uberculosis</i>
  作者：Mukund K. Gurjar、L. Krishnakanth Reddy、Srinivas Hotha

  DOI：10.1021/jo010180a

  日期：2001.6.1

  Syntheses of the ethyl glycosides of 5-O-(beta -D-galactofuranosyl)-beta -D-galactofuranose and 5-O-(alpha -D-arabinofuranosyl)-6-O-(beta -D-galactofuranosyl)-beta -D-galactofuranose present in motifs D and E of Mycobacterium tuberculosis arabinogalactan, respectively, have been presented. The pentenyl-mediated O-glycosylation reaction was utilized to obtain the disaccharide of motif D. The first coupling reaction to prepare the inner disaccharide portion of motif E was accomplished by trichloroacetamidate method while the installation of the terminal sugar by pentenyl glycosylation approach was successful.