Synthesis of carbohydrate-based surfactants
The present invention provides carbohydrate-based surfactants and methods for producing the same. Methods for producing carbohydrate-based surfactants include using a glycosylation promoter to link a carbohydrate or its derivative to a hydrophobic compound.
1. A method for producing a carbohydrate-based surfactant, said method consisting essentially of contacting a carbohydrate comprising a protecting group with a hydrophobic compound in the presence of a catalytic amount of a glycosylation promoter under conditions sufficient to form a covalent bond between said carbohydrate and said hydrophobic compound to produce a carbohydrate-based surfactant, wherein said hydrophobic compound comprises a functional group selected from the group consisting of an amine group, a hydroxyl group and a thiol group, and wherein the functional group of said hydrophobic compound covalently links said hydrophobic compound to said carbohydrate and wherein said glycosylation promoter is selected from the group consisting of bismuth (III) compound, a scandium (III) compound, an indium (III) compound and a mixture thereof.
2. The method of claim 1 , wherein said glycosylation promoter comprises a bismuth (III) compound.
3. The method of claim 2 , wherein said bismuth (III) compound comprises bismuth trifluoromethanesulfonate, bismuth halide, or a mixture thereof.
4. The method claim 1 , wherein the amount of glycosylation promoter used in the reaction is about 0.25 equivalent or less.
5. The method of claim 1 , wherein said hydrophobic compound is a hydrocarbon compound of the formula R x —X, wherein R x is a hydrocarbon and X is —OH, —NH 2 , or —SH.
6. The method of claim 5 , wherein R x is a C 6 -C 30 hydrocarbon.
7. The method of claim 6 , wherein R x is a C 6 -C 18 hydrocarbon.
8. The method of claim 1 further comprising a step of removing said protecting group to produce said carbohydrate-based surfactant.
9. The method of claim 1 , wherein said protecting group is a hydroxyl protecting group.
10. The method of claim 9 , wherein said hydroxyl protecting group comprises an ester.
11. The method of claim 9 , wherein said hydroxyl protecting group comprises acetate, benzoylate or a combination thereof.