Patent ID: 9090644
Filing Date: 2015-07-28
Classification: C07H

Abstract:
1. A process for synthesizing a lipochitooligosaccharide compound having the structure: where R 1 is selected from: H, and C 1 to C 20 alkyl, aryl, and aralkyl; R 2 and R 3 are independently C 1 to C 20 alkyl, aryl, aralkyl, C 2 to C 20 mono, di or polyalkenyl groups, or C 2 to C 20 mono, di or polyalkynyl, groups; and n is from 0 to about 20; comprising: a) providing a compound of structure D wherein R b) removing the ester groups and the N-phthalimido groups of non-silylated sugar unit of the compound of structure D by first removing the ester groups by transesterification and second removing N-phthalimido groups using an ethylenediamine Merrifield resin to form an amino-sugar product; c) selectively reacting the amino groups on the non-silylated sugar units of the amino-sugar product of b) with an acylating reagent to make an N-acyl derivative product; d) removing the silyl group on the silylated sugar unit of the N-acyl derivative product of c) by reacting the N-acyl derivative product with tetra-N-alkyl ammonium fluoride to produce a de-silylated product; e) removing the ester and the N-phthalimido group of the de-silylated product of d) by reacting the de-silylated product with an ethylenediamine Merrifield resin under refluxing conditions to produce a de-N-phthalimidated product; f) acylating the terminal amino group of the de-N-phthalimidated product of (e) with fatty acids activated with carbodiimide and N-hydroxylbenztriazole, or an acid halide of the formula R g) isolating the lipochitooligosaccharide.