OUVERTURE PAR LE N-BROMOSUCCINIMIDE DES ACETALS BENZYLIDENIQUES DE METHYL-HEXOSIDES DE CONFIGURATION MANNO ET SYNTHESE DE LA N-ACETYL-L-MYCOSAMINE

Article abstract of DOI:10.1016/S0008-6215(00)84674-1

Methyl 2,3:5,6-di-O-benzylidene-α-D-mannofuranoside and methyl 2,3-O-benzylidene-α-L-rhamnofuranoside were prepared according to a new procedure by simultaneous glycosidation and acetalation of D-mannose and L-rhamnose.Treatment of these compounds and of 1,6-anhydro-2,3-O-benzylidene-D-mannose with N-bromosuccinimide gave exclusively the 3-bromo compounds by regiospecific opening of the acetal ring.Thus, starting from rhamnose, N-acetyl-L-mycosamine (3-amino-3,6-dideoxy-L-mannose) was prepared in seven steps with a 32percent overall yield.