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A synthetic study of methyl 3-deoxy-3-fluoro-alpha-D-glucopyranosides from methyl 2,3-anhydro-alpha-D-allopyranosides, and synthesis of 3'-deoxy-3'-fluorokanamycin A and 3'-chloro-3'-deoxykanamycin A. 1992

E Umemura, and T Tsuchiya, and Y Kobayashi, and K Tanaka
Institute of Bioorganic Chemistry, Kawasaki, Japan.

Reactions of 4,6-disubstituted 2,3-anhydro-alpha-D-allopyranosides with potassium hydrogenfluoride (KHF2) in ethane-1,2-diol gave, by oxirane-ring opening, the corresponding 2-deoxy-2-fluoro-alpha-D-altro- and 3-deoxy-3-fluoro-alpha-D-gluco-pyranosyl derivatives, with the latter always in preponderance. The influence of the substituents at C-4 and C-6 on the D-gluco-D-altro ratio (r) have been studied by molecular mechanics, and the discrepancy between the experimental and calculated r values has been positively utilized to measure the effects of solvation and hydrogen bonding relative to the C-4 and C-6 substituents. By application of this reaction, 3'-deoxy-3'-fluorokanamycin A has been prepared by treatment of a 2',3'-anhydro-3'-epikanamycin A derivative (35) with KHF2. 3'-Chloro-3'-deoxykanamycin A was also prepared.

UI MeSH Term Description Entries
D007612 Kanamycin Antibiotic complex produced by Streptomyces kanamyceticus from Japanese soil. Comprises 3 components: kanamycin A, the major component, and kanamycins B and C, the minor components. Kanamycin A,Kanamycin Sulfate,Kantrex
D008969 Molecular Sequence Data Descriptions of specific amino acid, carbohydrate, or nucleotide sequences which have appeared in the published literature and/or are deposited in and maintained by databanks such as GENBANK, European Molecular Biology Laboratory (EMBL), National Biomedical Research Foundation (NBRF), or other sequence repositories. Sequence Data, Molecular,Molecular Sequencing Data,Data, Molecular Sequence,Data, Molecular Sequencing,Sequencing Data, Molecular
D002240 Carbohydrate Sequence The sequence of carbohydrates within POLYSACCHARIDES; GLYCOPROTEINS; and GLYCOLIPIDS. Carbohydrate Sequences,Sequence, Carbohydrate,Sequences, Carbohydrate

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