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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| Published in: | European journal of organic chemistry Vol. 2016; no. 16; pp. 2778 - 2784 |
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01-06-2016
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| Abstract | 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. |
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| AbstractList | 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 [alpha]/[beta] 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 [beta] 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. 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. 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. |
| Author | Ilyas, Saba Joseph, Troy W. De Castro, Michael Rosado, Luz M. Martin, Carla A. Meyerhoefer, Terence J. Bett, Saqib M. Bululu, Lubabalo |
| Author_xml | – sequence: 1 givenname: Luz M. surname: Rosado fullname: Rosado, Luz M. organization: Chemistry Department, Farmingdale State College-SUNY, 2350 Broadhollow Rd., NY, 11735, Farmingdale, USA – sequence: 2 givenname: Terence J. surname: Meyerhoefer fullname: Meyerhoefer, Terence J. organization: Chemistry Department, Farmingdale State College-SUNY, 2350 Broadhollow Rd., NY, 11735, Farmingdale, USA – sequence: 3 givenname: Saqib M. surname: Bett fullname: Bett, Saqib M. organization: Chemistry Department, Farmingdale State College-SUNY, 2350 Broadhollow Rd., NY, 11735, Farmingdale, USA – sequence: 4 givenname: Saba surname: Ilyas fullname: Ilyas, Saba organization: Chemistry Department, Farmingdale State College-SUNY, 2350 Broadhollow Rd., NY, 11735, Farmingdale, USA – sequence: 5 givenname: Lubabalo surname: Bululu fullname: Bululu, Lubabalo organization: Chemistry Department, Farmingdale State College-SUNY, 2350 Broadhollow Rd., NY, 11735, Farmingdale, USA – sequence: 6 givenname: Carla A. surname: Martin fullname: Martin, Carla A. organization: Chemistry Department, Farmingdale State College-SUNY, 2350 Broadhollow Rd., NY, 11735, Farmingdale, USA – sequence: 7 givenname: Troy W. surname: Joseph fullname: Joseph, Troy W. organization: Touro College, School of Health and Sciences, 1700 Union Blvd., NY, 11706, Bay Shore, USA – sequence: 8 givenname: Michael surname: De Castro fullname: De Castro, Michael email: michael.decastro@farmingdale.edu, Chemistry Department, Farmingdale State College-SUNY, 2350 Broadhollow Rd., Farmingdale, NY 11735, USA, michael.decastro@farmingdale.edu organization: Chemistry Department, Farmingdale State College-SUNY, 2350 Broadhollow Rd., NY, 11735, Farmingdale, USA |
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| Cites_doi | 10.1002/ejoc.201200130 10.1016/j.bmc.2005.08.010 10.1002/ejoc.200300483 10.1039/p19720002202 10.1042/bj0070207 10.1016/S0008-6215(82)80005-0 10.1002/anie.200351351 10.1007/BF00479966 10.1002/ejoc.201500001 10.1021/ja028694u 10.1021/ja0450298 10.1016/j.carres.2006.04.041 10.1021/ja026281n 10.1002/cber.19620951103 10.1021/ja00199a081 10.1080/07328303.2012.663431 10.1002/(SICI)1521-3773(20000103)39:1<204::AID-ANIE204>3.0.CO;2-Z 10.1016/j.carres.2008.01.045 10.1139/v65-298 10.1016/S0008-6215(00)85529-9 10.1002/ange.200351351 10.1071/CH08364 10.1016/0008-6215(95)00029-S 10.1016/j.crci.2010.09.004 10.1016/S0008-6215(98)00278-X 10.1021/jo0100751 10.1016/j.bmc.2004.07.013 10.1002/cber.190103401162 10.1021/jo060409s 10.1016/S0008-6215(00)84671-6 10.1021/ja803378k 10.1002/chem.19970030614 10.1042/bj0200195 10.1002/(SICI)1521-3757(20000103)112:1<210::AID-ANGE210>3.0.CO;2-U |
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| Snippet | 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... 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... |
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| SubjectTerms | Carbohydrates Glucuronamides Glycosylamides Synthetic methods |
| Title | Direct Coupling of Amides and Urea to Glycosyl Halides Using Silver Triflate |
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| Volume | 2016 |
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