Rotational isomerism in 6-β-D-glucopyranosides of methyl-1,2,6-thiadiazin-3(2H)-one 1,1-dioxides
- 1 January 1990
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 5,p. 783-786
- https://doi.org/10.1039/p29900000783
Abstract
Glucopyranosides of methyl-1,2,6-thiadiazin-3(2H)-one 1,1-dioxides have been synthesized and their rotational isomerism studied. Two of them exist, in solution, as mixtures of syn : anti rotamers, at room temperature. In the case of the diglucoside, the barriers to rotation about both glycosidic bonds have been calculated by dynamic 13C NMR.Keywords
This publication has 10 references indexed in Scilit:
- Synthesis of 2S-Dioxo Isosteres of Purine and Pyrimidine Nucleosides IV. Selective Glycosylation of 4-Amino-5H-Imidazo [4, 5-c]-1, 2, 6-Thiadiazine 2, 2-DioxideNucleosides, Nucleotides and Nucleic Acids, 1987
- Reactivity of 5-Methyl-2H -1,2,6-thiadiazin-3(6H )-one 1,1-Dioxide towards Alkylating Agents and CarbenesHETEROCYCLES, 1982
- NMR Studies on the syn‐anti Dynamic Equilibrium in Purine Nucleosides and NucleotidesEuropean Journal of Biochemistry, 1980
- Nucleotide Conformations: Rules and ExceptionsPublished by Springer Nature ,1979
- Synthesis of 2-S-dioxo isosters of purine and pyrimidine nucleosidesNucleic Acids Research, 1978
- Synthesis of nucleosides. 11. General synthesis of N-glycosides. III. Simple synthesis of pyrimidine disaccharide nucleosidesThe Journal of Organic Chemistry, 1974
- Nucleosides LXXVII. Rotational isomerism of certain 3-β-Tetrahedron Letters, 1972
- The reaction of sulfamide with diketene. Synthesis of an s‐dioxo analog of 6‐methyluracilJournal of Heterocyclic Chemistry, 1972
- Nucleoside und verwandte Verbindungen. VII. Alkylierung und Glykosidierung der Silyl-derivate 6-substituierter UracileCollection of Czechoslovak Chemical Communications, 1971
- Base pairing in DNAJournal of Molecular Biology, 1960