Synthesis of anellated carbasugars from (--)-quinic acid

Lidcay Herrera; Holger Feist; Manfred Michalik; José Quincoces; Klaus Peseke

doi:10.1016/s0008-6215(02)00411-1

Synthesis of anellated carbasugars from (--)-quinic acid

Carbohydr Res. 2003 Jan 31;338(3):293-8. doi: 10.1016/s0008-6215(02)00411-1.

Authors

Lidcay Herrera¹, Holger Feist, Manfred Michalik, José Quincoces, Klaus Peseke

Affiliation

¹ Fachbereich Chemie, Universität Rostock, D-18051, Rostock, Germany.

PMID: 12543563
DOI: 10.1016/s0008-6215(02)00411-1

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Carbohydrates / chemical synthesis*
Carbohydrates / chemistry
Molecular Mimicry*
Molecular Structure
Quinic Acid / chemistry*
Stereoisomerism

Substances

Carbohydrates
Quinic Acid