Enantioselective Synthesis of S-Linked Glycosyl-β2,2-Amino Acid Derivatives by SN2 Reaction with Hindered Sulfamidates

Alberto Avenoza; Jesús H. Busto; Gonzalo Jiménez-Osés; Jesús M. Peregrina

doi:10.1055/s-2006-926286

PAPER

Enantioselective Synthesis of S-Linked Glycosyl-β^2,2-Amino Acid Derivatives by S_N2 Reaction with Hindered Sulfamidates

Alberto Avenoza*, Jesús H. Busto, Gonzalo Jiménez-Osés, Jesús M. Peregrina*
Departamento de Química, Grupo de Síntesis Química de La Rioja, Universidad de La Rioja, U.A.-C.S.I.C., 26006 Logroño, Spain
Fax: +34(941)299655; e-Mail: alberto.avenoza@dq.unirioja.es;

Abstract

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Abstract

A new type of sugar-amino acid hybrid is presented and comprises of a sugar unit (mono- or disaccharide) α- or β-linked through an S-glycosidic linkage to the α-position of an α,α-disubstituted β-amino acid unit. The synthetic strategy is based on an S_N2 reaction between protected 1-thiosugars as nucleophiles and a hindered α-methylisoserine-derived sulfamidate as the chiral starting material.

Key words

amino acids - glycosylations - ring opening - steric hindrance - sulfur

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References

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