methyl (phenyl 5-acetamido-4,7,9-tri-O-benzyl-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-2-nonulopyranosid)onate | 1159257-98-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (phenyl 5-acetamido-4,7,9-tri-O-benzyl-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-2-nonulopyranosid)onate
• CAS: 1159257-98-3
• 化学式: C₃₉H₄₃NO₈S
• 分子量: 685.838
• InChiKey: FENPFXQNBOPLNW-ZUMKJCSBSA-N

物化性质

• 沸点：
  837.6±65.0 °C(predicted)
• 密度：
  1.27±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.69
• 重原子数：
  49.0
• 可旋转键数：
  16.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  112.55
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  methyl (phenyl 5-acetamido-4,7,9-tri-O-benzyl-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-2-nonulopyranosid)onate 、 碘甲烷 在 barium dihydroxide 、 barium(II) oxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 以72%的产率得到methyl (phenyl 5-acetamido-4,7,9-tri-O-benzyl-3,5-dideoxy-8-O-methyl-2-thio-D-glycero-β-D-galacto-2-nonulopyranosid)onate
  参考文献：
  名称：

  Synthesis of the starfish ganglioside LLG-3 tetrasaccharide

  摘要：

  The first synthesis of the ganglioside LLG-3 tetrasaccharide, which has attractive biological activities as well as a unique structure, is described. A C8-methoxy decorated sialic acid building block was initially prepared and a glycolic acid moiety was then introduced by sialylation. Amide condensation between the sialyl glycolic acid and an amino group at C5 on the sialyllactoside unit afforded the fully protected LLG-3 tetrasaccharide. Finally, the desired tetrasaccharide part of LLG-3 was obtained after careful global deprotection.[GRAPHICS](C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.02.003
• 作为产物：
  描述：

  methyl (phenyl 5-acetamido-8,9-O-benzylidene-4,7-di-O-benzyl-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-2-nonulopyranosid)onate 在 aluminum (III) chloride 、 borane-trimethylamine 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以72%的产率得到methyl (phenyl 5-acetamido-4,7,9-tri-O-benzyl-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-2-nonulopyranosid)onate
  参考文献：
  名称：

  Synthesis of the starfish ganglioside LLG-3 tetrasaccharide

  摘要：

  The first synthesis of the ganglioside LLG-3 tetrasaccharide, which has attractive biological activities as well as a unique structure, is described. A C8-methoxy decorated sialic acid building block was initially prepared and a glycolic acid moiety was then introduced by sialylation. Amide condensation between the sialyl glycolic acid and an amino group at C5 on the sialyllactoside unit afforded the fully protected LLG-3 tetrasaccharide. Finally, the desired tetrasaccharide part of LLG-3 was obtained after careful global deprotection.[GRAPHICS](C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.02.003