Dicyclohexylcarbodiimide → 6-(5-Cholesten-3beta-yloxy)hexyl 6-deoxy-6-oleamido-1-thio-beta-D-galactopyranoside

Participants

Reaction Steps

A solution of dicyclohexylcarbodiimide (106 mg.) in chloroform (5 ml.) is added to a solution of 6-(5-cholesten-3β-yloxy)hexyl 6-amino-6-deoxy-1-thio-β-D-galactopyranoside (309 mg.) and oleic acid (131.5 mg.) in chloroform (20 ml.). After 3 hours at room temperature, the reaction mixture is filtered and washed with water (20 ml.) and methanol (25 ml.). The organic layer is dried and evaporated in vacuo to a syrup which is crystallized from methanol to give the title compound (238 mg., 55%); m.p. 160°-163° C., [α]D27 -5.0° C. (C 1.0, chloroform).

Provenance & Evidence