Three different Mitsunobu reactions have been investigated for the synthesis of 1-deoxymannojirimycin (1-DMJ) from d-fructose. The highest yielding and most practical synthesis can be undertaken on a 10 g scale with minimal chromatography. In the key step, ,-di-Boc-hydroxylamine reacts with methyl 1,3-isopropylidene-α-d-fructofuranose under Mitsunobu conditions to give . Acidic hydrolysis affords nitrone , which reduces quantitatively via catalytic hydrogenolysis to afford 1-DMJ () in 55% overall yield from d-fructose (cf. 37% for azide route and 29% for nosyl route).
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