Direct Coupling of Amides and Urea to Glycosyl Halides Using Silver Triflate

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European Journal of Organic Chemistry, ISSN: 1099-0690, Vol: 2016, Issue: 16, Page: 2778-2784

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Luz M. Rosado; Terence J. Meyerhoefer; Saqib M. Bett; Saba. Ilyas; Lubabalo. Bululu; Carla A. Martin; Troy W. Joseph; Michael De Castro
Wiley; Touro Scholar
Chemistry; synthetic methods; carbohydrates; glycosylamides; glucuronamides; Organic Chemistry
article description
We herein report the coupling of various amides and ureas to glycosyl halides in the presence of silver triflate at room temperature. A 1:1 mixture of α/β diastereomers was obtained when alkyl/heteroaryl amides and substituted ureas were added to gluco and galacto haloglycosides. The effect of temperature, halogen, protecting group of the sugar and substituent of the amide in the overall yields and stereoselectivity of the reaction was also explored. When the acetyl-protected glucuronamide was employed in the reaction, the β anomer of the corresponding pseudodissacharide was obtained as the major isomer in good yields at room temperature. The newly synthesized compounds were subjected to viability studies using HeLa cancer cells. The results obtained are also discussed in this study.