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-ulopyranosidonic acid | 1091626-98-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 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-ulopyranosidonic acid
• 英文别名: prop-2-ynyl(-4)[prop-2-ynyl(-7)][prop-2-ynyl(-8)][Mob(-9)]NeuAc(b)-SPh；(2S,4S,5R,6R)-5-acetamido-6-[(1S,2R)-3-[(4-methoxyphenyl)methoxy]-1,2-bis(prop-2-ynoxy)propyl]-2-phenylsulfanyl-4-prop-2-ynoxyoxane-2-carboxylic acid
• CAS: 1091626-98-0
• 化学式: C₃₄H₃₇NO₉S
• 分子量: 635.735
• InChiKey: PYGYTAIMHDSNRS-POZLCQPYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  45
• 可旋转键数：
  17
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  147
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  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-ulopyranosidonic acid 、 三甲基硅烷化重氮甲烷 以 甲醇 、 乙醚 为溶剂， 反应 3.0h， 以95%的产率得到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
  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-acetamido-9-O-(p-methoxy)benzyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-non-2-ulopyranosid]onate 、 3-溴丙炔 在 barium hydroxide octahydrate 、 barium(II) oxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以50%的产率得到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-ulopyranosidonic acid
  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.