302579-04-0

Upstream product

• 445424-42-0 (4S,5R)-5-Benzyloxy-4-benzyloxymethyl-[1,3,2]dioxathiane 2-oxide 
• 92206-12-7 (2R,3S)-2,4-bis(benzyloxy)butane-1,3-diol 
• 302579-03-9 (4S,5R)-5-Benzyloxy-4-benzyloxymethyl-2,2-dimethyl-[1,3]dioxane 

Relevant academic research and scientific papers

Synthesis of selenium analogues of the naturally occurring glycosidase inhibitor salacinol and their evaluation as glycosidase inhibitors

The syntheses of two selenium analogues (10 and 11) of the naturally occurring sulfonium ion, salacinol (3), are described. Salacinol is one of the active principles in the aqueous extracts of Salacia reticulata that are traditionally used in Sri Lanka and India for the treatment of diabetes. The synthetic strategy relies on the nucleophilic attack of a 2,3,5-tri-O-benzyl-1,4-anhydro-4-seleno-D-arabinitol at the least hindered carbon of benzyl- or benzylidene-protected D- or L-erythritol-1,3-cyclic sulfate. The use of 1,1,1,3,3,3-hexafluoro-2-propanol as a solvent in the coupling reaction proves to be beneficial. Enzyme inhibition assays indicate that 10 is a better inhibitor (Ki = 0.72 mM) of glucoamylase than 3, which has a Ki value of 1.7 mM. In contrast, 11 showed no significant inhibition of glucoamylase. Compounds 10 and 11 showed no significant inhibition of barley-α-amylase or porcine pancreatic-α-amylase.

Synthesis of salacinol

Salacinol, a new type of α-glucosidase inhibitor discovered from the antidiabetic herb, was synthesized for the first time. Under the strategy that salacinol would be synthesized by the coupling reaction between 1,4-epithio-D-arabinitol and the cyclic sul