Sucrose based surfactants and methods thereof

A sulfonated sucrose having the structure:

• wherein R1 is benzoyl or substituted benzoyl and one of R2 and R3 is —SO3H and the other is selected from the group consisting of hydrogen and —SO3H.

A sulfonated sucrose having the structure:

• wherein R1 is a benzoyl or substituted benzoyl and R2 are R3 are different and are selected from the group consisting of hydrogen and —SO3H.

A surfactant having the structure:

• wherein R1 and R2 are different and are selected from the group consisting of hydrogen and —SO3H, and wherein n is 5 to 25.

A surfactant having the structure:

• wherein R1 and R2 are different and are selected from the group consisting of hydrogen and —SO3H, and wherein n i s 5 to 25 carbon atoms.

A surfactant having the structure:

• wherein R is selected from the group consisting of —OC(O)—(CH2)nCH3 and —NH+2—(CH2)nCH3 and n is an integer from 5 to 25.

An intermediate cyclic sulfate having the structure:

• wherein R is hydrogen or a hydroxyl protecting group selected from the group consisting of -Ac, -Bz, Bn, silyl.

An intermediate cyclic sulfite having the structure:

• wherein R is be hydrogen or a hydroxyl protecting group selected from the group consisting of -Ac, -Bz, Bn, silyl.

A process for synthesizing a 4,6-cyclic sulfite derivative of sucrose by reacting sucrose or 2,3,1′,3′,4′,6′-hexa-O-acetylsucrose with thionyl chloride in the presence of base.

A process for synthesizing a 4,6-cyclic sulfate derivative of sucrose by oxidizing a 4,6-cyclic sulfite derivative of sucrose with RuCl3(catalytic)/NaIO4.

A process for synthesizing a sucrose derivative that is 6-O-substituted with a nucleophilic reagent and is 4-O-sulfonated comprising opening a 4,6-cyclic sulfate sucrose or a derivative thereof with a nucleophile, wherein the nucleophile is selected from the group consisting of fatty acyl and aminoalkyl compounds containing from 4 to 30 carbons.