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

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 tempe...

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Bibliographic Details
Published in:	European journal of organic chemistry Vol. 2016; no. 16; pp. 2778 - 2784
Main Authors:	Rosado, Luz M., Meyerhoefer, Terence J., Bett, Saqib M., Ilyas, Saba, Bululu, Lubabalo, Martin, Carla A., Joseph, Troy W., De Castro, Michael
Format:	Journal Article
Language:	English
Published:	Weinheim Blackwell Publishing Ltd 01-06-2016 Wiley Subscription Services, Inc
Subjects:	Carbohydrates Glucuronamides Glycosylamides Synthetic methods
Online Access:	Get full text
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Summary:	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. Amides and ureas were coupled 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.
Bibliography:	Farmingdale State College istex:F147A57AF6059BFBE630EC88F982E3BB85C22B78 Supporting Information ark:/67375/WNG-DH9RJN1D-S ArticleID:EJOC201600350
ISSN:	1434-193X 1099-0690
DOI:	10.1002/ejoc.201600350