Synthesis of (±)-isofagomine and its stereoisomers from arecoline

Stereoelectronic Substituent Effects in Polyhydroxylated Piperidines and Hexahydropyridazines

“…Syntheses : Compounds (±)‐ 23 ,16 28 ,17 31 ,18 (±)‐ 32 ,18 (±)‐ 34 ,19 (±)‐ 35 ,19 (±)‐ 36 ,19 (±)‐ 37 ,19 38 ,20 40 ,36 41 ,18 (±)‐ 42 ,22 (±)‐ 43 ,22 44 ,19 45 ,19 (±)‐ 46 ,19 (±)‐ 65 ,23 66 ,14 and (±)‐ 67 23 were synthesized by previously published methods. Compounds 47, 48, 52 , and 54 24 were kindly provided by Professor Asano, and 53 by Professor Stütz.…”

A Free-Energy Relationship between the Rate of Acidic Hydrolysis of Glycosides and the pKa of Isofagomines

“…For example, in the conformationally restricted amines 5 and 6 , the isomer with an axial hydroxyl group was found to be the stronger base (Scheme ) 7. We also measured the p K a values of available9, 10 isofagomine analogues 7 – 10 and found a considerable variation (Scheme ). Furthermore, the p K a of 1‐deoxynojirimycin and its manno and galacto analogues were reported11 to be 6.3, 7.2, and 7.1, respectively.…”

A Free-Energy Relationship between the Rate of Acidic Hydrolysis of Glycosides and the pKa of Isofagomines

“…[7,8] For example, in the conformationally restricted amines 5 and 6, the isomer with an axial hydroxyl group was found to be the stronger base (Scheme 1). [7] We also measured the pK a values of available [9,10] isofagomine analogues 7 ± 10 and found a considerable variation (Scheme 1). Furthermore, the pK a of 1-deoxynojirimycin and its manno and galacto analogues were reported [11] to be 6.3, 7.2, and 7.1, respectively.…”