Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2012, Issue 4, Pages 744-753Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201101267
Keywords
Carbohydrates; Glycosides; Protecting groups; Synthetic methods
Categories
Funding
- National Science Council of Taiwan (NSC) [99-2113-M-001-010-MY2]
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A highly efficient TMSOTf-catalyzed HMDS silylation of sugars, which can easily be integrated with subsequent reactions in one-pot fashion, has been developed. Its usefulness was demonstrated by applications to streamlined regioselective one-pot protection and nonenzymatic acetylation of unprotected sugars. Monosaccharide and trehalose building blocks with orthogonally well-differentiated hydroxy groups were efficiently prepared starting with free sugars in one-pot fashion without the need for prior per-O-silylation.
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