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- 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.
- Authors
Rajasekaran, Parasuraman; Singh, Govind Pratap; Hassam, Mohammad; Vankar, Yashwant D.
- 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.
- Subjects
CARBOHYDRATE analysis; PINACOL rearrangement; PRINS reaction; BIOCHEMICAL substrates; KETALS; SUGARS; CARBOCATIONS; ALLYL alcohol
- Publication
Chemistry - A European Journal, 2016, Vol 22, Issue 51, p18383
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201604902