methyl 2,3,5-tri-O-tert-butyldimethylsilyl-6-O-tosyl-β-D-galactofuranoside | 1435894-94-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,5-tri-O-tert-butyldimethylsilyl-6-O-tosyl-β-D-galactofuranoside
• CAS: 1435894-94-2
• 化学式: C₃₂H₆₂O₈SSi₃
• 分子量: 691.162
• InChiKey: NMOSBXQIUMHNFK-JYJZCUDQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.24
• 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：
  0.81
• 拓扑面积：
  89.52
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  methyl 2,3,5-tri-O-tert-butyldimethylsilyl-6-O-tosyl-β-D-galactofuranoside 在 甲醇 、 sodium methylate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 52.0h， 生成 methyl 2,3,5-tri-O-tert-butyldimethylsilyl-6-thio-β-D-galactofuranoside
  参考文献：
  名称：

  Synthesis of the (1→6)-linked thiodisaccharide of galactofuranose: Inhibitory activity against a β-galactofuranosidase

  摘要：

  A new (1 -> 6)-linked thiodisaccharide formed by two galactofuranosyl units has been synthesized. Methyl (methyl alpha,beta-D-galactofuranosid) uronate was employed as the starting compound, which was per-O-silylated with TBSCl and reduced with LiAlH4 to afford methyl 2,3,5-tri-O-tert-butyldimethylsilyl-beta-D-galactofuranoside (2 beta) as a key precursor for the preparation of methyl per-O-tert-butyldimethylsilyl-6-thio-beta-D-galactofuranoside (12). The free thiol group of 12 was glycosylated and the product O-deprotected to afford the target beta-D-Galf-S-(1 -> 6)-beta-D-Galf-OMe (14). The conformations of this thiodisaccharide were preliminarily studied using combined theoretical calculations and NMR data. Furthermore, the glycomimetic 14 showed to be a competitive inhibitor of the beta-galactofuranosidase from Penicillum fellutanum (K-i = 3.62 mM). (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.02.057
• 作为产物：
  描述：

  methyl (methyl per-O-TBS-α,β-D-galactofuranoside)uronate 在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 24.5h， 生成 methyl 2,3,5-tri-O-tert-butyldimethylsilyl-6-O-tosyl-β-D-galactofuranoside
  参考文献：
  名称：

  Synthesis of the (1→6)-linked thiodisaccharide of galactofuranose: Inhibitory activity against a β-galactofuranosidase

  摘要：

  A new (1 -> 6)-linked thiodisaccharide formed by two galactofuranosyl units has been synthesized. Methyl (methyl alpha,beta-D-galactofuranosid) uronate was employed as the starting compound, which was per-O-silylated with TBSCl and reduced with LiAlH4 to afford methyl 2,3,5-tri-O-tert-butyldimethylsilyl-beta-D-galactofuranoside (2 beta) as a key precursor for the preparation of methyl per-O-tert-butyldimethylsilyl-6-thio-beta-D-galactofuranoside (12). The free thiol group of 12 was glycosylated and the product O-deprotected to afford the target beta-D-Galf-S-(1 -> 6)-beta-D-Galf-OMe (14). The conformations of this thiodisaccharide were preliminarily studied using combined theoretical calculations and NMR data. Furthermore, the glycomimetic 14 showed to be a competitive inhibitor of the beta-galactofuranosidase from Penicillum fellutanum (K-i = 3.62 mM). (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.02.057