title: An efficient synthesis of d-mannoheptulose via oxidation of an olefinated sugar with potassium permanganate in aqueous acetone.
abstract: An efficient three-step synthesis of d-mannoheptulose was successfully accomplished from 2,3,4,5,6-penta-O-benzyl-d-mannose. First, an olefinated sugar was prepared from 2,3,4,5,6-penta-O-benzyl-d-mannose via a Wittig reaction. Second, the key step, a 2-hydroxyoxirane product was unexpectedly obtained by oxidation of the olefinated sugar with potassium permanganate in aqueous acetone. Finally d-mannoheptulose was synthesized through debenzylation and hydrolysis in an overall yield of 39%.
authors.affiliation: Nanjing University of Science & Technology, China.
authors.forename: Jie
authors.initials: J
authors.lastname: Cheng
authors.forename: Zhijie
authors.initials: Z
authors.lastname: Fang
authors.forename: Song
authors.initials: S
authors.lastname: Li
authors.forename: Baohui
authors.initials: B
authors.lastname: Zheng
authors.forename: Yuhua
authors.initials: Y
authors.lastname: Jiang
mesh_terms: D000096:Acetone / Q000737:chemistry*; D008356:Mannoheptulose / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011196:Potassium Permanganate / Q000737:chemistry*
chemical_list: D011196:Potassium Permanganate; D000096:Acetone; D008356:Mannoheptulose