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Stereoselective Synthesis of α‐Glycosyl Azides by TMSOTf‐Mediated Ring Opening of 1,6‐Anhydro Sugars
Author(s) -
Lepage Mathieu L.,
Bodlenner Anne,
Compain Philippe
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201201580
Subject(s) - chemistry , ring (chemistry) , glycosyl , azide , stereoselectivity , click chemistry , alkyne , alcohol , combinatorial chemistry , stereochemistry , organic chemistry , catalysis
Access to α‐glycosyl azides in modest to high diastereoselectivity by way of TMSN 3 ring‐opening of 1,6‐anhydro sugars mediated by TMSOTf is reported. The reaction tolerates a wide variety of functional groups including alcohol, alkyne, azide and ester groups. The efficient synthesis of a pseudopentasaccharide in five steps from commercially available levoglucosan by way of a “click‐click” approach is presented to highlight the interest of the TMSN 3 ring‐opening reaction.