methyl 5-(N-acetylacetamido)-3,5-dideoxy-4,7,8-tri-O-propargyl-2-phenylsulfonyl-D-glycero-α-D-galacto-non-2-(9-oxaulopyranosidonate) 1',1'-diphenyl-5-methoxysalicylic alcohol acetal | 1091627-04-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二恶烷
• 英文名称: methyl 5-(N-acetylacetamido)-3,5-dideoxy-4,7,8-tri-O-propargyl-2-phenylsulfonyl-D-glycero-α-D-galacto-non-2-(9-oxaulopyranosidonate) 1',1'-diphenyl-5-methoxysalicylic alcohol acetal
• 英文别名: methyl (2S,4S,5R,6R)-2-(benzenesulfonyl)-5-(diacetylamino)-6-[(1S,2S)-2-(6-methoxy-4,4-diphenyl-1,3-benzodioxin-2-yl)-1,2-bis(prop-2-ynoxy)ethyl]-4-prop-2-ynoxyoxane-2-carboxylate
• CAS: 1091627-04-1
• 化学式: C₄₉H₄₇NO₁₃S
• 分子量: 889.977
• InChiKey: CRMGNVOFTOCXGI-HZRADCMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  64
• 可旋转键数：
  17
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  171
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  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) 、 methyl 5-(N-acetylacetamido)-3,5-dideoxy-4,7,8-tri-O-propargyl-2-phenylsulfonyl-D-glycero-α-D-galacto-non-2-(9-oxaulopyranosidonate) 1',1'-diphenyl-5-methoxysalicylic alcohol acetal 在 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 反应 0.08h， 以70%的产率得到methyl (2S,4S,5R,6R)-5-(diacetylamino)-2-[(1R,2R,3S)-3-[(2R,3R,4S,6S)-3-(diacetylamino)-6-methoxycarbonyl-6-phenylsulfanyl-4-prop-2-ynoxyoxan-2-yl]-1-hydroxy-2,3-bis(prop-2-ynoxy)propyl]-6-[(1S,2S)-2-(6-methoxy-4,4-diphenyl-1,3-benzodioxin-2-yl)-1,2-bis(prop-2-ynoxy)ethyl]-4-prop-2-ynoxyoxane-2-carboxylate
  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 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以85%的产率得到methyl 5-(N-acetylacetamido)-3,5-dideoxy-4,7,8-tri-O-propargyl-2-phenylsulfonyl-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

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.