2,3,4,6-tetra-O-acetyl-alpha-D-mannopyranosyl azide → (2R,3R,4S,5S,6R)-2-(Acetoxymethyl)-6-aminotetrahydro-2H-pyran-3,4,5-triyl triacetate

Participants

Reaction Steps

To a mixture of about 3.0 grams of 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl azide, 0.5 grams Raney nickel catalyst, and 40 ml. ethyl acetate, is vigorously agitated with hydrogen at atmospheric pressure, at a temperature of about 25° C. for a period of about 6.5 hours. The reaction mixture is filtered through diatomaceous silica, and the filtered solution is evaporated in vacuo to a syrup which crystallizes upon standing at a temperature of about 5° C. The crystalline product is recrystallized from 2-propanol to give about 1.7 grams of 2,3,4,6-tetra-O-acetyl-β-D-mannopyranosylamine; m.p. 145°-147° C.; [α]D25 -9.8° (c 1.02, methanol).

Provenance & Evidence