methyl 4,6-O-benzylidene-3-O-(chloroacetyl)-β-D-galactopyranosyl-(1->4)-O-β-D-glucopyranoside | 874479-74-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4,6-O-benzylidene-3-O-(chloroacetyl)-β-D-galactopyranosyl-(1->4)-O-β-D-glucopyranoside
• CAS: 874479-74-0
• 化学式: C₂₂H₂₉ClO₁₂
• 分子量: 520.918
• InChiKey: GIAMYNOMEUVZLO-JYDTYHSASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.19
• 重原子数：
  35.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  162.6
• 氢给体数：
  4.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  methyl 4,6-O-benzylidene-3-O-(chloroacetyl)-β-D-galactopyranosyl-(1->4)-O-β-D-glucopyranoside 在 吡啶 、 4-二甲氨基吡啶 、 4 A molecular sieve 、 乙酸肼 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 methyl 2-O-benzoyl-4,6-O-benzylidene-β-D-galactopyranosyl-(1->4)-O-2,3,6-tri-O-benzoyl-β-D-glucopyranoside
  参考文献：
  名称：

  The synthesis and biological evaluation of lactose-based sialylmimetics as inhibitors of rotaviral infection

  摘要：

  Rotaviruses are the most significant cause of gastroenteritis in young children and are responsible for over 600,000 infant deaths annually. The rotaviral haemagglutinin protein (VP8*) of some strains has been implicated in early recognition and binding events of host cell-surface sialoglycoconjugates, and is therefore an attractive target for potential therapeutic intervention. Since N-acetylneuraminic acid alpha(2,3)-linked to galactose is believed to be the minimum binding epitope of rotavirus to host cells, we report here our development of an efficient and flexible synthetic route to a range of lactose-based sialylmimetics of alpha(2,3)-linked thiosialosides. These compounds were biologically evaluated as inhibitors of rotaviral infection using an in vitro neutralisation assay. The results suggest that these lactose-based sialylmimetics are not inhibitors of the rhesus rotavirus strain; however, they do exhibit modest inhibition of the human (Wa) strain, presumably through inhibition of the rotaviral adhesion process. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.08.057
• 作为产物：
  描述：

  methyl 4-O-(4,6-O-benzylidene-β-D-galactopyranosyl)-β-D-glucopyranoside 、 氯乙酰氯 在 二正丁基氧化锡 、 4 A molecular sieve 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 2.5h， 以70%的产率得到methyl 4,6-O-benzylidene-3-O-(chloroacetyl)-β-D-galactopyranosyl-(1->4)-O-β-D-glucopyranoside
  参考文献：
  名称：

  The synthesis and biological evaluation of lactose-based sialylmimetics as inhibitors of rotaviral infection

  摘要：

  Rotaviruses are the most significant cause of gastroenteritis in young children and are responsible for over 600,000 infant deaths annually. The rotaviral haemagglutinin protein (VP8*) of some strains has been implicated in early recognition and binding events of host cell-surface sialoglycoconjugates, and is therefore an attractive target for potential therapeutic intervention. Since N-acetylneuraminic acid alpha(2,3)-linked to galactose is believed to be the minimum binding epitope of rotavirus to host cells, we report here our development of an efficient and flexible synthetic route to a range of lactose-based sialylmimetics of alpha(2,3)-linked thiosialosides. These compounds were biologically evaluated as inhibitors of rotaviral infection using an in vitro neutralisation assay. The results suggest that these lactose-based sialylmimetics are not inhibitors of the rhesus rotavirus strain; however, they do exhibit modest inhibition of the human (Wa) strain, presumably through inhibition of the rotaviral adhesion process. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.08.057