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Synthesis 2009(24): 4143-4148  
DOI: 10.1055/s-0029-1217045
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Stereoselective Synthesis of Novel N-β-Glycosyl Sulfonamides by Sulfonamidoglycosylation of Per-O-acetylated Sugars

Pedro Alfonso Colinas*, Carlos Agustín Témpera, Oscar Mariano Rodríguez, Rodolfo Daniel Bravo
LADECOR, Departamento de Química, Facultad de Ciencias Exactas, Universidad Nacional de La Plata, 47 y 115 (1900) La Plata, Argentina
Fax: +54(221)4226947; e-Mail: pcolinas@quimica.unlp.edu.ar;
Further Information

Publication History

Received 17 July 2009
Publication Date:
19 October 2009 (online)

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Abstract

A series of novel N-glycosyl sulfonamides is prepared by sulfonamidoglycosylation of per-O-acetylated sugars. The products which contain an unnatural sulfonamide moiety at the anomeric centre are obtained in very good yields and with excellent β-stereoselectivity, even with per-O-acetylated d-mannose.

Key words

sulfonamidoglycosylation - per-O-acetylated carbohydrates - sulfonamides - β-stereoselectivity - exo-anomeric effect

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11

de Bravo, M. G. [INIBIOLP (UNLP-CONICET), Fac. Cs. Médicas] personal communication.

18

¹H and ¹³C NMR spectra of the crude reaction mixtures showed only the presence of β-sulfonamidomanno-pyranoside and unreacted per-O-acetylated manno-pyranoside.