Enantiospecific syntheses of deoxymannojirimycin, fagomine and 2r,5r-dihydroxymethyl-3r,4r-dihydroxypyrrolidine from D-glucose

Add time:07/28/2019    Source:sciencedirect.com

Methyl 2-azido-3-O-benzyl-2-deoxy-α-D-mannofuranoside (4), readily available from D-glucose, is a common intermediate in the enantiospecific syntheses of deoxymannojirimycin [1,5-dideoxy-1,5-imino-D-mannitol](l), fagomine [1,2,5-trideoxy-1,5-imino-D- arabino hexitol] (2) and 2R,5R-dihydroxymethyl-3R,4R-dihydroxypyrrolidine (3); these syntheses establish the absolute configurations of (2) and (3).

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