Synthesis of Fluorous Photolabile Aldehyde and Carbamate and Alkyl Carbamate Protecting Groups for Carbohydrate-Associated Amines

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...

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Bibliographic Details
Published in:Organic letters 2014-02, Vol.16 (4), p.1156-1159
Main Authors: Roychoudhury, Rajarshi, Pohl, Nicola L. B
Format: Article
Language:English
Subjects:
Aldehydes - chemical synthesis
Aldehydes - chemistry
Amines - chemistry
Carbamates - chemical synthesis
Carbamates - chemistry
Indicators and Reagents
Letter
Molecular Structure
Oligosaccharides - chemical synthesis
Oligosaccharides - chemistry
Solid Phase Extraction
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol500023y