methyl (2-propenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2,3,5-trideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosid)onate | 143131-47-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (2-propenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2,3,5-trideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosid)onate
• 英文别名: methyl (2-propenyl)-5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosidonate；allyl (methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosid) onate；methyl (2S,4S,5R,6R)-5-acetamido-4-acetyloxy-2-prop-2-enylsulfanyl-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
• CAS: 143131-47-9
• 化学式: C₂₃H₃₃NO₁₂S
• 分子量: 547.581
• InChiKey: HRYUJBDLRZIFPU-JTCPLQINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  37
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  195
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  methyl (2-propenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2,3,5-trideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosid)onate 在 sodium hydroxide 、 sodium methylate 作用下， 以 甲醇 为溶剂， 以65%的产率得到sodium (2S)-2-propenyl 5-acetamido-2,3,5-trideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosidonic acid
  参考文献：
  名称：

  Towards the synthesis of sialic acid-based Salmonella typhimurium sialidase inhibitors

  摘要：

  DOI：

  10.1016/0008-6215(95)00128-g
• 作为产物：
  描述：

  2-Thiosialic acid methyl ester peracetate 、 3-溴丙烯 在 二乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以95%的产率得到methyl (2-propenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2,3,5-trideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosid)onate
  参考文献：
  名称：

  一种制备N-乙酰神经氨酸硫糖苷的简单方法。

  摘要：

  DOI：

  10.1016/0008-6215(94)84064-4

文献信息

• Mild stereoselective syntheses of thioglycosides under PTC conditions and their use as active and latent glycosyl donors
  作者：Suoding Cao、Serge J. Meunier、Fredrik O. Andersson、Marie Letellier、René Roy

  DOI：10.1016/s0957-4166(00)86308-9

  日期：1994.11

  Mild and stereoselective arylthio glycoside syntheses were accomplished by inversion of configuration of glycosyl halides under phase transfer catalyzed conditions. Under such conditions, aryl alpha-thiosialosides having electron donating and withdrawing substituents were evaluated as active and latent thioglycosyl donors. A sialyl-alpha-(2-->6)-galactoside was prepared in good yield using the above strategy.
• Facile Preparation of Divalent Sialoside Derivatives by Olefin Metathesis Reaction
  作者：Zhonghong Gan、René Roy

  DOI：10.1016/s0040-4020(00)00034-x

  日期：2000.3

  Olefin metathesis catalyzed by RuCl2(CHPh)(PCy3)(2) (1) has been used to synthesize homodimers of O- and S-alkenyl alpha-sialoside derivatives. The reactions afforded reasonable to good yields under mild reaction conditions. Trans-geometrical isomers were preferred in all cases. (C) 2000 Elsevier Science Ltd. All rights reserved.