Sulfonamidoglycosylation of methyl ribofuranosides: A novel approach to furanosylsulfonamides

Tetrahedron Letters

Volumn 46, Issue 10, 2005, Pages 1687-1689

  Colinas, Pedro A ^a   Bravo, Rodolfo D ^a  

^a UNIVERSIDAD NACIONAL DE LA PLATA   (Argentina)

Author keywords

Lewis acids; Methyl glycosides; Sulfonamidoglycosides; Sulfonamidoglycosylation

Indexed keywords

AMIDE; METHYL GROUP; SULFONAMIDE;

ARTICLE; CATALYST; CHEMICAL MODIFICATION; CHEMICAL REACTION KINETICS; DRUG SYNTHESIS; GLYCOSYLATION; QUANTUM YIELD;

EID: 13744260946     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.01.065     Document Type: Article

References (20)

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16. General procedure: To a solution or suspension of the methyl glycoside (1 mmol), the sulfonamide (1.5 mmol), and 500 mg of MS 4 A (beads) in 5 mL of dry methylenechloride was added, under argon, 1 mmol of boron trifluoride etherate at room temperature. After stirring for the time indicated, the mixture was quenched with 0.3 mL of triethylamine. The solvent was removed in vacuo and the residue was chromatographed on silica gel (eluent hexane/ethyl acetate) and/or crystallized (ethyl acetate/hexane) to afford the sulfonamidoglycosides
17. The sulfonamidoglycosylation with sulfamide in methylenechloride afforded the N,N′-substituted product. This result can be explained in terms of the low concentration of sulfamide in the solution due to their poor solubility. When a better solvent was used (such as acetonitrile) the reaction gave the corresponding N-monosubstituted sulfamide
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