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Synthesis of Fluorous Photolabile Aldehyde and Carbamate and Alkyl Carbamate Protecting Groups for Carbohydrate-Associated Amines
- Roychoudhury, Rajarshi, Pohl, Nicola L. B.
- Organic letters 2014 v.16 no.4 pp. 1156-1159
- aldehydes, chemical reactions, chemical structure, oligosaccharides, secondary amines, solid phase extraction
- Two new fluorous photolabile-protecting groups (FNBC and FNB) and a new base-labile protecting group (FOC) for the masking of amines are reported. The protecting groups survive a wide range of common reaction conditions used in oligosaccharide synthesis and render the attached molecules amenable to fluorous solid-phase extraction (FSPE). A glycosyl acceptor containing the FNB group is shown to be useful in the synthesis of carbohydrates tagged with free deactivated secondary amines.