methyl 2,3,4-tri-O-acetyl-6-thio-6-[2'-(methyl butanoate)]-β-D-glucopyranoside | 357952-97-7

• 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 2,3,4-tri-O-acetyl-6-thio-6-[2'-(methyl butanoate)]-β-D-glucopyranoside
• 英文别名: methyl 2-[[(2S,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-methoxyoxan-2-yl]methylsulfanyl]butanoate
• CAS: 357952-97-7
• 化学式: C₁₈H₂₈O₁₀S
• 分子量: 436.48
• InChiKey: LCFKGIDOZWCYIL-YYHPLQAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  29
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  149
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4-tri-O-acetyl-6-thio-6-[2'-(methyl butanoate)]-β-D-glucopyranoside 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 15.0h， 生成 methyl 6-thio-6-[2'-(butanoic acid)]-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Sialylmimetics as Rotavirus Inhibitors

  摘要：

  Rotaviruses cause severe gastroenteritis in infants and are estimated to be responsible for over 600 000 deaths annually, primarily in developing countries. The development of potential inhibitors of this virus is therefore of great interest, particularly since the safety and efficacy of rotaviral vaccines has recently been questioned. This study describes the synthesis of a variety of compounds that can be considered as mimetics of N-acetylneuraminic acid thioglycosides and the subsequent in vitro biological evaluation of these sialylmimetics as inhibitors of rotaviral infection. Our results show that readily accessible carbohydrate-based compounds have the potential to act as inhibitors of rotaviral replication in vitro, presumably through inhibition of the rotaviral adhesion process.

  DOI：

  10.1021/jm0100887
• 作为产物：
  描述：

  methyl 2,3,4-tri-O-acetyl-6-O-p-toluenesulfonyl-β-D-glucopyranoside 在 乙酸肼 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 52.5h， 生成 methyl 2,3,4-tri-O-acetyl-6-thio-6-[2'-(methyl butanoate)]-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of Novel Sialylmimetics as Biological Probes

  摘要：

  Glycomimetics are increasingly being recognised as powerful tools in the search for novel compounds that possess useful biological properties. This paper describes our preliminary efforts towards the development of novel mimetics of sialic acid thioglycosides. These sialylmimetics are readily prepared and have been shown, in some instances, to have biological properties similar to sialic acid thioglycosides. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00276-1