(S)-benzyl 2-{[(benzyloxy)carbonyl]amino}-5-[(2-{[alpha-D-mannopyranosyl-(1->3)-[alpha-D-mannopyranosyl-(1->6)]-alpha-D-mannopyranosyl]oxy}ethyl)amino]-5-oxopentanoate → (S)-2-amino-5-((2-((alpha-D-mannopyranosyl-(1->3)-[alpha-D-mannopyranosyl-(1->6)]-alpha-D-mannopyranosyl)oxy)ethyl)amino)-5-oxopentanoic acid

Participants

Reaction Steps

A mixture of (S)-benzyl 2-{[(benzyloxy)carbonyl]amino}-5-[(2-{[α-D-mannopyranosyl-(1→3)-[α-D-mannopyranosyl-(1→6)]-α-D-mannopyranosyl]oxy}ethyl)amino]-5-oxopentanoate (1.0 g, 1.11 mmol) and Pd/C (118 mg, 0.111 mmol) in water (10 mL) was allowed to stir under a balloon of H2 at room temperature for 16 hours. The catalyst was filtered off and washed with H2O (3×10 mL). The filtrate was concentrated to give the title compound. UPLC Method B: calculated for C25H44N2O19 676.25, observed m/e: 677.21 [M+1]; Rt=0.86 min.

Provenance & Evidence