title: γ-Aminoalcohol rearrangement applied to pentahydroxylated azepanes provides pyrrolidines epimeric to homoDMDP.
abstract: A series of pentahydroxylated pyrrolidines, displaying five contiguous stereogenic centres and epimeric to α-glucosidase inhibitor homoDMDP, have been synthesized. The key step involves a γ-aminoalcohol rearrangement applied to polyhydroxylated azepanes. These five-membered iminosugars demonstrate micromolar inhibition of glycosidases.
authors: Glycochemistry Group of "Organic Synthesis" Team, Université de Poitiers, UMR-CNRS 7285 IC2MP, 4 rue Michel Brunet, 86073 Poitiers Cedex 9, France. yves.bleriot@univ-poitiers.fr.
authors: Y
authors: Y
authors: Jagadeesh
authors: A T
authors: AT
authors: Tran
authors: B
authors: B
authors: Luo
authors: N
authors: N
authors: Auberger
authors: J
authors: J
authors: Désiré
authors: S
authors: S
authors: Nakagawa
authors: A
authors: A
authors: Kato
authors: Y
authors: Y
authors: Zhang
authors: M
authors: M
authors: Sollogoub
authors: Y
authors: Y
authors: Blériot
mesh_terms: D000605:Amino Alcohols / Q000737:chemistry*; D001381:Azepines / Q000737:chemistry*; D065089:Glycoside Hydrolase Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D050112:Imino Pyranoses / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D008353:Mannitol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D015394:Molecular Structure; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry; D013329:Structure-Activity Relationship; D000520:alpha-Glucosidases / Q000378:metabolism
chemical_list: C494911:2,5-dideoxy-2,5-imino-D-mannitol; D000605:Amino Alcohols; D001381:Azepines; D065089:Glycoside Hydrolase Inhibitors; D050112:Imino Pyranoses; D011759:Pyrrolidines; D008353:Mannitol; D000520:alpha-Glucosidases