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Reaction of Trimethylsilyl Azide with Anhydro Sugars, a Mild Method of Oxirane‐Ring Opening
Author(s) -
Janairo Gerardo,
Kowollik Wolfgang,
Voelter Wolfgang
Publication year - 1987
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.198719870211
Subject(s) - trimethylsilyl azide , chemistry , nucleophile , azide , trimethylsilyl , yield (engineering) , ring (chemistry) , lewis acids and bases , organic chemistry , catalysis , materials science , metallurgy
Lewis acid catalyzed reactions of trimethylsilyl azide with the anhydro sugars 1–3 yield isomeric mixtures of the corresponding unsilylated azidodeoxy sugars 4–9 . This procedure is mild, convenient, and does not displace nucleophile‐sensitive groups.