Valienamine → HCID 131719634, compound

Participants

Reaction Steps

A solution of protected valienamine, (1R)-(1,2,4/3)-2,3,4-tribenzyl-5-benzyloxy-methylcyclohex-5-enylamine, (Compound 1) made according to the method of Ogawa et al. J. Chem. Soc. Perkin Trans (1988)3 (1.41 g, 2.63 mmol). This was combined with the protected epoxide, 1,6-anhydro-4-O-benzyl-2,3-epoxy-glucose, made according to the method set forth in Cerny et al., J. Czechoslav. Chem. Commun 39 (1974)4 (compound 2) (3.28 g, 14.0 mmol), in n-propanol (28 ml) and was heated at 90° C. for 4 days. Solvent was evaporated, then co-evaporated with toluene and the residue was chromatographed on a silica gel column using hexane:ethylacetate (2:1) as eluent to provide 1,6-anhydro-4-O-benzyl-2-deoxy-2-[1D-(1N,2,4/3)-(2,3,4-tri-O-benzyl-5-C-benzyloxymethyl-2,3,4-trihydroxy-5-cyclohexen-1-yl)amino]-β-D-glucopyranose (compound 3) (1.2 g, 59.2%).

Provenance & Evidence