title: Aza-Claisen rearrangement of 2-C-hydroxymethyl glycals as a versatile strategy towards synthesis of isofagomine and related biologically important azasugars.
abstract: Synthesis of isofagomine has been achieved by implementation of aza-Claisen rearrangement of 2-C-hydroxymethyl glycals as a key step. The above rearrangement has also been utilized in the synthesis of biologically important polyhydroxylated piperidine frameworks such as isogalactofagomine, ent-isogalactofagomine and their analogues and some other azasugars as glycosidase inhibitors.
authors.affiliation: Department of Chemistry, Indian Institute of Technology, Kanpur 208 016, India.
authors.forename: Y Suman
authors.initials: YS
authors.lastname: Reddy
authors.forename: Pavan K
authors.initials: PK
authors.lastname: Kancharla
authors.forename: Rashmi
authors.initials: R
authors.lastname: Roy
authors.forename: Yashwant D
authors.initials: YD
authors.lastname: Vankar
mesh_terms: D001372:Aza Compounds / Q000737:chemistry*; D002241:Carbohydrates / Q000737:chemistry*; D004986:Ether / Q000737:chemistry*; D006900:Hydroxylation; D050112:Imino Pyranoses / Q000138:chemical synthesis*; D008745:Methylation; D015394:Molecular Structure
chemical_list: D001372:Aza Compounds; D002241:Carbohydrates; D050112:Imino Pyranoses; C098432:isofagomine; D004986:Ether