ethyl 2,3,6-tri-O-benzyl-β-D-galactofuranoside | 352463-48-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2,3,6-tri-O-benzyl-β-D-galactofuranoside
• 英文别名: (1R)-1-[(2S,3S,4R,5R)-5-ethoxy-3,4-bis(phenylmethoxy)oxolan-2-yl]-2-phenylmethoxyethanol
• CAS: 352463-48-0
• 化学式: C₂₉H₃₄O₆
• 分子量: 478.585
• InChiKey: HBHRFKFXMVMZDW-JYJZCUDQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  35
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  ethyl 2,3,6-tri-O-benzyl-β-D-galactofuranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 4 A molecular sieve 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 26.0h， 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
• 作为产物：
  描述：

  溴甲苯 、 ethyl 2,3-di-O-benzyl-β-D-galactofuranoside 在 二正丁基氧化锡 、 四丁基溴化铵 作用下， 以 甲苯 为溶剂， 反应 30.0h， 以71%的产率得到ethyl 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.