title: A Cascade "Prins-Pinacol-Type Rearrangement and C4-OBn Participation" on Carbohydrate Substrates: Synthesis of Bridged Tricyclic Ketals, Annulated Sugars and C2-Branched Heptoses.
abstract: A "Prins pinacol type rearrangement followed by C4-OBn participation" in a cascade manner has been observed while probing the fate of carbocation in some carbohydrate derived homoallylic alcohols in the Prins reaction. This has led to an easy access to tetrahydrofuran-fused bridged bicyclic ketals (or tetrahydrofuran-fused 1,6-anhydro-heptopyranose frameworks) which are further converted into some annulated sugars and C2-branched heptoses.
authors: Department of Chemistry, Indian Institute of Technology, Kanpur, 208016, India.
authors: Parasuraman
authors: P
authors: Rajasekaran
authors: Department of Chemistry, Indian Institute of Technology, Kanpur, 208016, India.
authors: Govind Pratap
authors: GP
authors: Singh
authors: Department of Chemistry, Indian Institute of Technology, Kanpur, 208016, India.
authors: Mohammad
authors: M
authors: Hassam
authors: Department of Chemistry, Indian Institute of Technology, Kanpur, 208016, India.
authors: Yashwant D
authors: YD
authors: Vankar
mesh_terms: D002241:Carbohydrates / Q000138:chemical synthesis* / Q000737:chemistry; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D006539:Heptoses / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D002241:Carbohydrates; D005663:Furans; D006539:Heptoses; D011083:Polycyclic Compounds; C018674:tetrahydrofuran
keywords: 1,6-anhydro-heptopyronoses; 2c-branched sugars; annulated sugars; cyclization; rearrangement