Regioselective synthesis of fatty acid esters of methyl α-D-glucopyranoside with dibutyltin dimethoxide method and biological test against staphylococcus aureus and salmonella agona

Xin Lou, Julie O'Brien, Gary Henehan, Seamas Cassidy

Research output: Contribution to journalArticlepeer-review

Abstract

Fatty acid esters of methyl α-D-glucopyranoside were regioselectively synthesized using dibutyltin dimethoxide (DBDM) as stannylating agent, general factors affecting regioselectivity has been examined. Comparison work indicated that DBDM has some advantage as stannylating agent over dibutyltin oxide for regioselective acylation at the 2-position of unprotected methyl α-D-glucopyranoside. Microbiological tests show that methyl 2-lauryl-α-D-glucopyranoside is effective inhibitor against gram-negative bacterial Staphylococcus aures.

Original languageEnglish
Pages (from-to)3135-3146
Number of pages12
JournalAsian Journal of Chemistry
Volume22
Issue number4
Publication statusPublished - 2010

Keywords

  • Antibacterial
  • Dibutyltin dimethoxide
  • Fatty acid esters of carbohydrates
  • Regioselectivity

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