ethyl (E)-3-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosylthio)-acrylate | 1330066-51-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl (E)-3-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosylthio)-acrylate
• 英文别名: ethyl (E)-3-[(2R,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]sulfanylprop-2-enoate
• CAS: 1330066-51-7
• 化学式: C₃₉H₄₂O₇S
• 分子量: 654.824
• InChiKey: ZQONPEDBHXZEIW-PLTFJEODSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  47
• 可旋转键数：
  18
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  97.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  (2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-thiol 、 丙炔酸乙酯 在 三乙烯二胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 ethyl (Z)-3-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosylthio)-acrylate 、 ethyl (E)-3-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosylthio)-acrylate
  参考文献：
  名称：

  Synthesis of Glycosylthiols and Reactivity Studies

  摘要：

  The acid-catalyzed reaction of 1,2-anhydro-3,4,6-tri-O-benzyl-alpha-D-glucopyranose (7) as glycosyl donor with bis-trimethylsilyl sulfide as acceptor affords the alpha-thiol. Hence, this sterically hindered S-nucleophile as acceptor should provide with O-glycosyl trichloroacetimidates as glycosyl donors that have nonparticipating groups at C-2, glycosylthiols with the thiol group in axial position. This was confirmed for various donors (4, 16-19) with the exception of the corresponding mannosyl donor (20). However, powerful participating groups at C-2 of the donor (23-28) governed the anomeric selectivity.

  DOI：

  10.1021/jo200624e