|
| << previous | next >> |
Journal description
All volumes of the corresponding journal
All issues of the corresponding volume
All articles of the corresponding issues
Details for article 3 of 10 found articles
| Title: |
Chemical Modification of Kanamycin A. II. Nucleophilic Displacement Reactions of Kanamycin-A-4''-sulfonates |
| Author: |
Albert, R. Dax, K. Stutz, A. E. Weidmann, H. |
| Appeared in: |
Journal of carbohydrate chemistry |
| Paging: | Volume 1 (1982) nr. 3 pages 289-299 |
| Year: |
1982-01-01 |
| Contents: |
Reactions of 2',3',4',2'',6''-penta-O-acetyl-tetra-N-tert-butyloxycarbonyl-kanamycin-A-4''-brosylate (4b) or-4''-triflate (4c) with acetate, thiolacetate, azide, and fluoride, respectively, result in the formation of the corresponding derivatives of 4''-epi-kanamycin A (5a-d). While 4b invariably forms an elimination byproduct (9), the only side—reaction of 4c consists in a neighboring group attack with formation of a 3''-epi-4''-cyclic urethane (7). Removal of the protecting groups yields 4''-epi-(6a), 4''-thio-4''-epi-(6b), 4''-deoxy-4''-fluoro-4''-epi-(6d), 4''-azido-4''-deoxy-4''-epi-(6c), and after hydrogenation of the latter, 4''-amino-4''-deoxy-4''-epi-kanamycin A (6f). Methyl 2,6-di-O-acetyl-3-amino-3-N-tert-butyloxycarbonyl-3-deoxy-4-O-triflyl-β-D-glucopyranoside (1b) served as a model to anticipate preparation, handling, and reactivity of 4c. |
| Publisher: |
Taylor & Francis |
| Source file: |
Elektronische Wetenschappelijke Tijdschriften |
Details for article 3 of 10 found articles
| << previous | next >> |