title: Synthesis of anellated carbasugars from (--)-quinic acid.
abstract: (3R,4R,5R)-3-[(tert-Butyl-dimethylsilyl)oxy]-4,5-(isopropylidenedioxy)-1-cyclohexanone (2) reacted with carbon disulfide and methyl iodide in the presence of sodium hydride to furnish (3R,4R,5R)-5-[(tert-butyl-dimethylsilyl)oxy]-3,4-(isopropylidenedioxy)-2-[bis(methylthio)methylene]-1-cyclohexanone (3). 2 and N,N-dimethylformamide dimethyl acetal afforded (2E,3R,4R,5R)-5-[(tert-butyl-dimethylsilyl)oxy]-2-(dimethylaminomethylene)-3,4-(isopropylidenedioxy)-1-cyclohexanone (4). These push-pull activated methylenecyclohexanones 3 and 4 underwent a ring closure reaction with hydrazine hydrate and methylhydrazine, respectively, to give pyrazoloanellated carbasugars. Treatment of 3 with formamidinium, acetamidinium and benzamidinium salts, respectively, in the presence of sodium methanolate yielded three (5R,6R,7R)-7-[(tert-butyl-dimethylsilyl)oxy]-5,6,7,8-tetrahydro-5,6-(isopropylidenedioxy)benzo[d]pyrimidines.
authors.affiliation: Fachbereich Chemie, Universität Rostock, D-18051, Rostock, Germany.
authors.forename: Lidcay
authors.initials: L
authors.lastname: Herrera
authors.forename: Holger
authors.initials: H
authors.lastname: Feist
authors.forename: Manfred
authors.initials: M
authors.lastname: Michalik
authors.forename: José
authors.initials: J
authors.lastname: Quincoces
authors.forename: Klaus
authors.initials: K
authors.lastname: Peseke
mesh_terms: D002241:Carbohydrates / Q000138:chemical synthesis* / Q000737:chemistry; D018716:Molecular Mimicry; D015394:Molecular Structure; D011801:Quinic Acid / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D002241:Carbohydrates; D011801:Quinic Acid