methyl phenyl 5-(N-acetylacetamido)-9-O-(p-methoxybenzyl)-3,5-dideoxy-4,7,8-tri-O-propargyl-2-thio-D-glycero-α-D-galacto-non-2-ulopyranosidonate | 1091627-00-7

• 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)-9-O-(p-methoxybenzyl)-3,5-dideoxy-4,7,8-tri-O-propargyl-2-thio-D-glycero-α-D-galacto-non-2-ulopyranosidonate
• 英文别名: methyl (2S,4S,5R,6R)-5-(diacetylamino)-6-[(1S,2R)-3-[(4-methoxyphenyl)methoxy]-1,2-bis(prop-2-ynoxy)propyl]-2-phenylsulfanyl-4-prop-2-ynoxyoxane-2-carboxylate
• CAS: 1091627-00-7
• 化学式: C₃₇H₄₁NO₁₀S
• 分子量: 691.799
• InChiKey: XXHTXFFZORNJHV-FIUAYTJISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  49
• 可旋转键数：
  18
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  144
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  methyl phenyl 5-(N-acetylacetamido)-9-O-(p-methoxybenzyl)-3,5-dideoxy-4,7,8-tri-O-propargyl-2-thio-D-glycero-α-D-galacto-non-2-ulopyranosidonate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以75%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-ulopyranosidonate
  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：

  乙酸异丙烯酯 、 methyl phenyl 5-acetamido-9-O-(p-methoxybenzyl)-3,5-dideoxy-4,7,8-tri-O-propargyl-2-thio-D-glycero-α-D-galacto-non-2-ulopyranosidonate 在 对甲苯磺酸 作用下， 反应 5.0h， 以96%的产率得到methyl phenyl 5-(N-acetylacetamido)-9-O-(p-methoxybenzyl)-3,5-dideoxy-4,7,8-tri-O-propargyl-2-thio-D-glycero-α-D-galacto-non-2-ulopyranosidonate
  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.