Tetrahedron p. 5863 - 5876 (1997)
Update date:2022-08-04
Topics:
Aguilera, Begona
Fernandez-Mayoralas, Alfonso
Jaramillo, Carlos
A cyclic 2,3-sulfamidate derived from N-acetyl-D-allosamine has been treated with a variety of S-. N-, O-. and C-nucleophiles, leading to nucleophilic displacement at C-3, elimination, or deacetylation reactions depending on the type of nucleophile used. Nucleophilic displacement is achieved with thio-nucleophiles and NaN3. allowing the preparation of 3-thio- or 3-azido glucosamine derivatives difficult to obtain by use of sulfonates.
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