The preparation of 2-iodoamides from glucals and their further transformations into oxazolines |
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Authors: | Michael De Castro |
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Affiliation: | Department of Chemistry and Biochemistry, Seton Hall University, 400 South Orange Ave., South Orange, NJ 07079, USA |
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Abstract: | 2-Deoxy-2-iodo-glycosylamides have been prepared from a variety of protected d-glucals by their reaction with N-iodosuccinimide and amides. Benzyl protected 2-iodoamides, when treated with sodium hydride and 15-crown-5, gave stable C1 N-linked 2-glycooxazolines as the major products. Silyl protected 2-iodoamides afforded the C1 O-linked 2-glycooxazolines; presumably by the rearrangement of unstable N-acylaziridine intermediates. |
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Keywords: | Iodoamidation Glucals 2-Glycooxazolines |
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