Amiprilose [ l,2-O-isopropylidene-3-O-(3-N,N-dimethylaminopropyl)-ce-D-glucofur-
anose] (1) and its hydrochloride salt [Therafectin "~ (SM1213)] are synthetic carbohydrates [1,2] known to exhibit antiproliferative and anti-inflammatory activities [3][4][5][6]. Compound 1 acts as an immunomodulator [7] and therefore has a therapeutic effect on such autoimmune disorders as arthritis, psoriasis, eczema, and systemic lupus erythematosus [3][4][5][6]. It has low toxicity and no serious side effects [8,9], but is required in large doses for effective therapy. This presents a problem for oral administration of such a drug, especially since treatment of inflammatory or autoimmune disorders is often mid-to long-term. Attempts have been made by other workers [1,6,10,11] to discover a more potent derivative of this drug. For example, a few 6-thio derivatives of D-glucose, partially or fully protected by isopropylidene groups such as 4a and 4e, were recently prepared. Preliminary investigations showed that they are approximately 5-1000 times more potent than the parent compound [6,10,11]. This prompted us to report a simpler route for 4c and the synthesis of new 3-thio derivatives of 1, as a part of our studies on thioethers derived from various sugars [12,13]. For this purpose a two-step strategy was used in which starting protected monosaccharides were converted into iodides and then condensed with the appropriate tertiary aminoalkanethiolates to give the desired thioethers.