REACTIONS OF 3,4,6-TRI-O-ACETYL-2-AMINO-2-DEOXY-D-GLUCOPYRANOSYL AZIDE WITH HETEROCUMULENES.

摘要

3,4,6-Tri-O-acetyl-2-amino-2-deoxy-D-glucopyranosyl azide (2), a versatile chiron that can easily be obtained from D-glucosamine (1), enables the preparation of other functionalized aminosugars. Thus, condensation of 2 with aryl isocyanates and isothiocyanates produces the corresponding ureas and thioureas (3), which further react with triphenylphosphine leading to glycosyl phosphonimines 5. These substances can also be generated from 4. On the other hand, the treatment of compound 4 with carbon disulfide gives rise to the zwitterionic derivative 6 in high yield.