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Synlett 2000; 2000(9): 1253-1256
DOI: 10.1055/s-2000-7161
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A New Synthetic Method for α- and β-Glycosyl Ureas and its Application to the Synthesis of Glycopeptide Mimics with Urea-glycosyl Bonds

Yoshiyasu Ichikawa* , Taihei Nishiyama, Minoru Isobe
  • *Laboratory of Organic Chemistry, School of Bioagricultural Sciences, Nagoya University, Chikusa, Nagoya 464-8601, Japan
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Publication Date:
31 December 2000 (online)

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A new procedure for the stereospecific synthesis of α- and β-glycosyl isocyanates by oxidation of glycosyl isocyanides has been developed. The reaction of α- and β-glucosyl isocyanates with amines proceeds smoothly to provide α- and β-glucosyl ureas with a net retention of the stereochemistry at the anomeric position. This method offers the synthesis of a building block for the glycopeptide mimics with urea-glycosyl linkages.

amines - azides - carbohydrate - glycosyl isocyanate - urea

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