methyl 4,6-O-benzylidene-3-O-(chloroacetyl)-β-D-galactopyranoside | 874479-73-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: methyl 4,6-O-benzylidene-3-O-(chloroacetyl)-β-D-galactopyranoside
• 英文别名: methyl 3-O-chloroacetyl-4,6-O-benzylidene-β-D-galactopyranoside
• CAS: 874479-73-9
• 化学式: C₁₆H₁₉ClO₇
• 分子量: 358.776
• InChiKey: CXOGVAKUBDFNCP-IYOGYMKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.98
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  83.45
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  methyl 4,6-O-benzylidene-3-O-(chloroacetyl)-β-D-galactopyranoside 在 吡啶 、 乙酸肼 、 四丁基亚硝酸铵 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 6.0h， 生成 methyl 2-O-benzoyl-4,6-O-benzylidene-3-O-trifluoromethanesulfonyl-β-D-gulopyranoside
  参考文献：
  名称：

  Galactose‐Phosphonates as Mimetics of the Sialyltransfer by Trypanosomal Sialidases

  摘要：

  In an attempt to find competitive inhibitors of the trans- sialidase of the pathogen Trypanosoma cruzi, we have synthesized conjugates of carbocyclic sialylmimetics ( e. g., cyclohexenephosphonates) and galactose derivatives. A trans- sialidase inhibition assay revealed an interesting preference for ethylidene- spacered conjugates involving the 3- position of the sugar.

  DOI：

  10.1080/07328300701351532
• 作为产物：
  描述：

  氯乙酰氯 、 methyl 4,6-O-(S)-benzylidene-β-D-galactopyranoside 在 吡啶 作用下， 以 乙腈 为溶剂， 以37%的产率得到methyl 4,6-O-benzylidene-3-O-(chloroacetyl)-β-D-galactopyranoside
  参考文献：
  名称：

  Galactose‐Phosphonates as Mimetics of the Sialyltransfer by Trypanosomal Sialidases

  摘要：

  In an attempt to find competitive inhibitors of the trans- sialidase of the pathogen Trypanosoma cruzi, we have synthesized conjugates of carbocyclic sialylmimetics ( e. g., cyclohexenephosphonates) and galactose derivatives. A trans- sialidase inhibition assay revealed an interesting preference for ethylidene- spacered conjugates involving the 3- position of the sugar.

  DOI：

  10.1080/07328300701351532

文献信息

• The synthesis and biological evaluation of lactose-based sialylmimetics as inhibitors of rotaviral infection
  作者：Angela Liakatos、Milton J. Kiefel、Fiona Fleming、Barbara Coulson、Mark von Itzstein

  DOI：10.1016/j.bmc.2005.08.057

  日期：2006.2

  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.