2,4,6-tri-O-acetyl-3-O-(2,3,5,6-tetra-O-acetyl-β-D-galactofuranosyl)-α-D-mannopyranose | 1438222-98-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,4,6-tri-O-acetyl-3-O-(2,3,5,6-tetra-O-acetyl-β-D-galactofuranosyl)-α-D-mannopyranose
• CAS: 1438222-98-0
• 化学式: C₂₆H₃₆O₁₈
• 分子量: 636.561
• InChiKey: KTBUMBRFCVSAGE-WIHUUPPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  44.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  232.02
• 氢给体数：
  1.0
• 氢受体数：
  18.0

反应信息

• 作为反应物：
  描述：

  2,4,6-tri-O-acetyl-3-O-(2,3,5,6-tetra-O-acetyl-β-D-galactofuranosyl)-α-D-mannopyranose 、 三氯乙腈 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以83.4%的产率得到(2R,3R,4S,5S)-2-(acetoxymethyl)-4-(((2S,3R,4S,5S)-3,4-diacetoxy-5-((R)-1,2-diacetoxyethyl)tetrahydrofuran-2-yl)oxy)-6-(2,2,2-trichloro-1-iminoethoxy)tetrahydro-2H-pyran-3,5-diyl diacetate
  参考文献：
  名称：

  Synthetic tools for the characterization of galactofuranosyl transferases: glycosylations via acylated glycosyl iodides

  摘要：

  With the aim of developing synthetic tools for the characterization of galactofuranosyltransferases, the synthesis of 9-decenyl glycosides of D-Manp, D-Galf, and beta-D-Galf-(1 -> 3)-D-Manp was targeted. The interest in the alkenyl aglycone arises via potential conjugation reactions, once the terminal double bond has been conveniently functionalized. The glycosylation of beta-D-Galf-(1 -> 3)-D-Manp was attempted by two different approaches: the trichloroacetimidate method and the glycosylation via the glycosyl iodide. The conditions for the latter were established on the basis of glycosylation assays of per-O-acetylmannose. On the other hand, the study of glycosylation reactions via per-O-benzoylated galactofuranosyl iodide confirms the versatility of glycosyl iodides as donors. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.03.032
• 作为产物：
  描述：

  C₂₈H₃₈O₁₉ 在 溶剂黄146 、 乙二胺 作用下， 以 四氢呋喃 为溶剂， 反应 21.0h， 以84%的产率得到2,4,6-tri-O-acetyl-3-O-(2,3,5,6-tetra-O-acetyl-β-D-galactofuranosyl)-α-D-mannopyranose
  参考文献：
  名称：

  Synthetic tools for the characterization of galactofuranosyl transferases: glycosylations via acylated glycosyl iodides

  摘要：

  With the aim of developing synthetic tools for the characterization of galactofuranosyltransferases, the synthesis of 9-decenyl glycosides of D-Manp, D-Galf, and beta-D-Galf-(1 -> 3)-D-Manp was targeted. The interest in the alkenyl aglycone arises via potential conjugation reactions, once the terminal double bond has been conveniently functionalized. The glycosylation of beta-D-Galf-(1 -> 3)-D-Manp was attempted by two different approaches: the trichloroacetimidate method and the glycosylation via the glycosyl iodide. The conditions for the latter were established on the basis of glycosylation assays of per-O-acetylmannose. On the other hand, the study of glycosylation reactions via per-O-benzoylated galactofuranosyl iodide confirms the versatility of glycosyl iodides as donors. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.03.032