2-benzamido-tetra-0-benzoyl-2-deoxy ammonolysis

The same compounds isolated by Brigl and coworkers,9 who started from 2,3,4,5,6,7-hexa-O-benzoyl-D-gZt/cero-D-gaZacto-heptononitriIe, were obtained from the ammonolysis of 1,2,3,4,6-penta-O-benzoyl-a-D-mannose,19 namely, a mixture of l,l-bis(benzamido)-l-deoxy-D-mannitol (12) and N-benzoyl-D-mannopyranosylamine (13). Likewise, 1,2,3,4-tetra-O-benzoyl-L-rhamnopyranose,10 having the same steric relationship at the asymmetric carbon atoms as the perbenzoate of D-mannose, also afforded an N-benzoyl-L-rhamnopyranosylamine directly. 

An experiment whose results support certain mechanistic views (see Section VI, p. 110) was the ammonolysis of 2,3,4,6-tetra-O-benzoyl-D-glucopyranosylamine,30 which afforded a mixture of D-glucose and D-glucosylamine in 95% yield, and only 1.4% of l,l-bis(benzamido)-l-deoxy-D-glucitol (17) with traces of N-benzoyl-D-glucopyranosylamine. 

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