To valorize further the highly valuable bio-based platform (S)-γ-hydroxymethyl-γ-butyrolactone (2H-HBO), whose sustainable kiloscale-synthesis from cellulose-derived levoglucosenone (LGO) has been validated, a mechanochemical strategy was developped to produce new potential bio-based surfactants in solventless conditions. First, the reaction of 2H-HBO with primary or secondary amines was investigated followed by a sulfation reaction on the isolated N-alkyl-amide derivatives to obtain the corresponding N-alkyl sulfated compounds. These latter were then obtained by an optimized one-pot sequential aminolysis-sulfation in a planetary ball mill with excellent efficiency. For the first time, sulfated compounds arising from biobased/renewable ressources were obtained exclusively via a mechanochemical process. As a result, these sulfated derivatives of 2H-HBO were formed quantitatively and isolated in 69-79% overall yields. Critical micellar concentration (CMC) was evaluated for some of them and revealed an interesting anionic surfactant properties.