C2-Acetamidomannosylation. Synthesis of 2-N-acetylamino-2-deoxy-α-d-mannopyranosides with glucal donors |
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| Authors: | Jing LiuValeria Di Bussolo David Y Gin |
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| Institution: | Department of Chemistry, University of Illinois at Urbana-Champaign, Urbana, IL 61801, USA |
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| Abstract: | A one-pot C2-acetamidomannosylation reaction for the synthesis of 2-N-acetylamino-2-deoxy-α-d-mannopyranosides from glucals is described. Glucal donors are activated by the reagent combination of 2,8-dimethyldibenzothiophene-5-oxide (DMDBTO) and trifluoromethanesulfonic anhydride. Upon subsequent addition of N-(TMS)acetamide and an appropriate glycosyl acceptor, the corresponding C2-acetamidomannopyranosides are formed. |
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| Keywords: | acetamidomannosylation glycosylation nitrogen transfer |
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