Improved synthesis of 6-amino-6-deoxy-d-galactono-1,6-lactam and d-mannono-1,6-lactam from corresponding unprotected d-hexono-1,4-lactones |
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| Authors: | Ludovic Chaveriat,Gilles Demailly,Daniel Beaupè re |
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| Affiliation: | Laboratoire des Glucides, Université de Picardie Jules Verne, 33 Rue Saint-Leu, F-80039 Amiens, France |
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| Abstract: | Regioselective bromination of unprotected d-galactono-1,4-lactone and d-mannono-1,4-lactone with PPh3/CBr4 led to 6-bromo-6-deoxy derivatives. These intermediates were treated with LiN3 and hydrogenated to give 6-amino-6-deoxy-d-galactono-1,6-lactam (8) and 6-amino-6-deoxy-d-mannono-1,6-lactam (13) in 74 and 67% overall yield, respectively. |
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| Keywords: | smallcaps" >d-galactono-1,4-lactone smallcaps" >d-mannono-1,4-lactone 6-Bromo-6-deoxy- smallcaps" >d-hexono-1,4-lactones Seven-member azasugars 6-Amino-6-deoxy- smallcaps" >d-galactono smallcaps" >d-mannono-1,6-lactams |
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