methyl phenyl 5-(N-acetylacetamido)-3,5-dideoxy-4,7,8-tri-O-propargyl-2-thio-D-glycero-α-D-galacto-non-2-(9-oxaulopyranosidonate) | 1091627-02-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl phenyl 5-(N-acetylacetamido)-3,5-dideoxy-4,7,8-tri-O-propargyl-2-thio-D-glycero-α-D-galacto-non-2-(9-oxaulopyranosidonate)
• 英文别名: methyl (2S,4S,5R,6R)-5-(diacetylamino)-6-[(1S,2S)-3-oxo-1,2-bis(prop-2-ynoxy)propyl]-2-phenylsulfanyl-4-prop-2-ynoxyoxane-2-carboxylate
• CAS: 1091627-02-9
• 化学式: C₂₉H₃₁NO₉S
• 分子量: 569.632
• InChiKey: IDWAGSLXEURARE-MSDMEXNYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  40
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  143
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2-(hydroxydiphenylmethyl)-4-methoxyphenol 、 methyl phenyl 5-(N-acetylacetamido)-3,5-dideoxy-4,7,8-tri-O-propargyl-2-thio-D-glycero-α-D-galacto-non-2-(9-oxaulopyranosidonate) 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 24.0h， 以83%的产率得到methyl phenyl 5-(N-acetylacetamido)-3,5-dideoxy-4,7,8-tri-O-propargyl-2-thio-D-glycero-α-D-galacto-non-2-(9-oxaulopyranosidonate) 1',1'-diphenyl-5-methoxysalicylic alcohol acetal
  参考文献：
  名称：

  Stereoselective Synthesis of a C-Linked Neuraminic Acid Disaccharide: Potential Building Block for the Synthesis of C-Analogues of Polysialic acids

  摘要：

  C-Linked neuraminic acid disaccharide was synthesized in a diastereoselective manner from a sulfone donor and aldehyde acceptor, which was protected as a propargyl ether, through a samarium-mediated coupling reaction. The resulting disaccharide has acetal and phenyl sulfide functional C groups that can be easily converted into aldehyde and phenyl sulfone groups by photolysis and oxidation reactions to serve as disaccharide acceptor and donor, respectively.

  DOI：

  10.1021/jo801946y
• 作为产物：
  描述：

  methyl phenyl 5-(N-acetylacetamido)-3,5-dideoxy-4,7,8-tri-O-propargyl-2-thio-D-glycero-α-D-galacto-non-2-(9-oxaulopyranosidonate) 1',1'-diphenyl-5-methoxysalicylic alcohol acetal 以 乙腈 为溶剂， 反应 1.33h， 以60%的产率得到methyl phenyl 5-(N-acetylacetamido)-3,5-dideoxy-4,7,8-tri-O-propargyl-2-thio-D-glycero-α-D-galacto-non-2-(9-oxaulopyranosidonate)
  参考文献：
  名称：

  Stereoselective Synthesis of a C-Linked Neuraminic Acid Disaccharide: Potential Building Block for the Synthesis of C-Analogues of Polysialic acids

  摘要：

  C-Linked neuraminic acid disaccharide was synthesized in a diastereoselective manner from a sulfone donor and aldehyde acceptor, which was protected as a propargyl ether, through a samarium-mediated coupling reaction. The resulting disaccharide has acetal and phenyl sulfide functional C groups that can be easily converted into aldehyde and phenyl sulfone groups by photolysis and oxidation reactions to serve as disaccharide acceptor and donor, respectively.

  DOI：

  10.1021/jo801946y

文献信息

• Stereoselective Synthesis of a <i>C</i>-Linked Neuraminic Acid Disaccharide: Potential Building Block for the Synthesis of <i>C</i>-Analogues of Polysialic acids
  作者：Jin-Hwan Kim、Fei Huang、Mellisa Ly、Robert J. Linhardt

  DOI：10.1021/jo801946y

  日期：2008.12.5

  C-Linked neuraminic acid disaccharide was synthesized in a diastereoselective manner from a sulfone donor and aldehyde acceptor, which was protected as a propargyl ether, through a samarium-mediated coupling reaction. The resulting disaccharide has acetal and phenyl sulfide functional C groups that can be easily converted into aldehyde and phenyl sulfone groups by photolysis and oxidation reactions to serve as disaccharide acceptor and donor, respectively.