Enzymatic synthesis of fructose-based sugar fatty acid esters, such as methyl fructoside oleic acid mono and diester, was investigated using methyl fructoside as a sugar starting material. For the production of methyl fructoside fatty acid monoester by solvent process, 2-methyl 2-propanol was found to be a god reaction medium resulting a higher yield and productivity due to its high sugar solubility. The yield and productivity of methyl fructoside oleic acid monoester were 70% and 12.6g/L-hr, respectively, when molar ratio of methyl fructoside, initial concentration of methyl fructoside, enzyme(Novozym 435) content, and reaction temperature were 3:1, 200g/L, 1%(w/v), and $60^{circ}C$, respectively. Methyl fructoside oleic acid diester was prepared by lipase-catalyzed diacylation of methyl fructoside and oleic acid in the solvent-free process. Maximum yield of 98% and productivity of 140g/L-hr were achieved when molar ratio(methyl fructoside and oleic acid) of 1:2 enzyme content of 10%(w/v) and reaction temperature of $70^{circ}C$ were applied for the operating conditions under a reduced pressure of 20∼200 mmHg.