phenyl (5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonylopyranosyl)-(2->3)-β-D-galactopyranosyl-(1->4)-1-thio-β-D-glucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl (5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonylopyranosyl)-(2->3)-β-D-galactopyranosyl-(1->4)-1-thio-β-D-glucopyranoside
• 英文别名: sodium;N-[(2R,3R,4S,6S)-6-carboxy-6-[(2S,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6S)-4,5-dihydroxy-2-(hydroxymethyl)-6-phenylsulfanyloxan-3-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-4-hydroxy-2-[(1R,2R)-1,2,3-trihydroxypropyl]oxan-3-yl]ethanimidate
• 化学式: C₂₉H₄₂NO₁₈S*Na
• 分子量: 747.704
• InChiKey: NHPQSNIRKCNTIA-CTDRCORASA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -8.78
• 重原子数：
  50
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  347
• 氢给体数：
  11
• 氢受体数：
  20

反应信息

• 作为反应物：
  描述：

  苯甲酸酐 、 phenyl (5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonylopyranosyl)-(2->3)-β-D-galactopyranosyl-(1->4)-1-thio-β-D-glucopyranoside 在 吡啶 作用下， 反应 44.0h， 以44%的产率得到phenyl [(5-acetamido-4,8,9-tri-O-benzoyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonylopyranosyl-1'->2-lactone)]-(2->3)-O-4,6-di-O-benzoyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzoyl-1-thio-β-D-glucopyranoside
  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：

  N-乙酰神经氨酸水合物 、 β-phenylsulfanyl lactoside 在 CMP-Neu₅Ac synthetase 、 Neu5Acα(2->3) transferase 、 胞苷-5’-三磷酸 作用下， 生成 phenyl (5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonylopyranosyl)-(2->3)-β-D-galactopyranosyl-(1->4)-1-thio-β-D-glucopyranoside
  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

文献信息

• Ready Access to Sialylated Oligosaccharide Donors
  作者：Seema Mehta、Michel Gilbert、Warren W. Wakarchuk、Dennis M. Whitfield

  DOI：10.1021/ol990406k

  日期：2000.3.1

  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.