phenyl [(5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonylopyranosyl-1'->2-lactone)]-(2->3)-O-4,6-di-O-acetyl-1-thio-β-D-galactopyranoside | 263711-96-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl [(5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonylopyranosyl-1'->2-lactone)]-(2->3)-O-4,6-di-O-acetyl-1-thio-β-D-galactopyranoside
• 英文别名: [(2S,4'S,4aR,5S,5'R,6'R,7R,8S,8aS)-5'-acetamido-4',8-diacetyloxy-3-oxo-5-phenylsulfanyl-6'-[(1S,2R)-1,2,3-triacetyloxypropyl]spiro[5,7,8,8a-tetrahydro-4aH-pyrano[3,4-b][1,4]dioxine-2,2'-oxane]-7-yl]methyl acetate
• CAS: 263711-96-2
• 化学式: C₃₅H₄₃NO₁₈S
• 分子量: 797.788
• InChiKey: IVAWGFMCMQPKGO-JSAVMQNCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  55
• 可旋转键数：
  19
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  266
• 氢给体数：
  1
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  phenyl [(5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonylopyranosyl-1'->2-lactone)]-(2->3)-O-4,6-di-O-acetyl-1-thio-β-D-galactopyranoside 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 甲醇 为溶剂， 反应 40.0h， 生成 phenyl [methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonylopyranosyl)onate]-(2->3)-O-2,4,6-tri-O-acetyl-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  Ready Access to Sialylated Oligosaccharide Donors

  摘要：

  Numerous glycoconjugates contain the disaccharide Neu5Ac alpha(2-->3)DGalp. An efficient way to incorporate this disaccharide into synthetic glycoconjugates is to develop a disaccharide building block. This communication reports a chemoenzymatic route to such a building block which requires as few as four steps. Some examples using more chemical steps are also presented, which increase the flexibility. These disaccharide donors were used to prepare synthetic trisaccharides.

  DOI：

  10.1021/ol990406k
• 作为产物：
  描述：

  乙酸酐 、 phenyl (5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonylopyranosyl)-(2->3)-1-thio-β-D-galactopyranoside 在 吡啶 作用下， 反应 44.0h， 以75%的产率得到phenyl [(5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonylopyranosyl-1'->2-lactone)]-(2->3)-O-4,6-di-O-acetyl-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  Ready Access to Sialylated Oligosaccharide Donors

  摘要：

  Numerous glycoconjugates contain the disaccharide Neu5Ac alpha(2-->3)DGalp. An efficient way to incorporate this disaccharide into synthetic glycoconjugates is to develop a disaccharide building block. This communication reports a chemoenzymatic route to such a building block which requires as few as four steps. Some examples using more chemical steps are also presented, which increase the flexibility. These disaccharide donors were used to prepare synthetic trisaccharides.

  DOI：

  10.1021/ol990406k