Nucleosides 1 -methyl 2 -deoxy-, synthesis

For synthesis of nucleosides, methyl 4-acetamido-2,3-di-0-benzoyl-4-deoxy-a-D-ribopyranoside (198c), obtained from 198a, was trans-formed by acetolysis into 4-acetamido-l,5-di-0-acetyl-2,3-di-0-benzoyl-4-deoxy-D-ribofuranose (199b). Either with preliminary treatment with hydrogen chloride in acetyl chloride, or directly, in the presence of titanium tetrachloride, 199b gave with chloromercuri-(6-... 

Kotick MP, Klein RS. Watanabe KA, Fox JJ. Nucleosides. LXIl. Synthetic studies on nucleoside antibiotics. 2. Synthesis of methyl 4-amino-4-deoxy-D-glucosiduronic acid derivatives related to the carbohydrate moiety of gougerotin. Carbohydr Res 1969 11 369-377. Coutsogeorgopoulos C, Bloch A, Watanabe KA, Fox JJ. Inhibitors of protein synthesis. 4-Studies of the structure-activity relationship of gougerotin and some of its analogs. J Med Chem 1975 18 771-776. 

The reaction of cyclic thiocarbonates with methyl iodide (Chapter 13) and the use of 5 -deoxy-5 -iodo-nucleosides in the synthesis of unsaturated nucleosides (Chapter 14) are reported elsewhere. 

Xylopyranoside, methyl 3-amino-3-deoxy-a-D-, deamination of, in nucleoside synthesis, 70... 

Synthesis of 6-Chloro-9-(6 -deoxy-3 -C-methyl-2, 3, 4 -tri-0-methyl-/3-D-allopyrano-syl)purine A Branched-chain Sugar Nucleoside, G. B. Howarth, W. A. Szarek, and J. 

Benhida described the synthesis of a 2-deoxy-C-nucleoside analogue and its phosphoramidite derivative featuring 6-(thiazolyl-5)-a-benzimidazole nucleobase (134). A more efficient route to the expanded adenosine analogue (135) was developed by Kool, who also described the synthesis of the expanded thymidine analogue (136) starting from 5-methylanthranilic acid. Both nucleosides were found to be efficient fluorophores. 3 -Cyanoethyl phosphoramidites of 6-methyl-3-(2 -deoxy-(3-D-ribofuranosyl)-3//-pyrrolo[2,3-d]pyrimidin-2-one... 

Purines, pyrimidines and their nucleosides and nucleoside triphosphates are synthesized in the cytoplasm. At this stage the antifolate drugs (sulphonamides and dihydrofolate reductase inhibitors) act by interfering with the synthesis and recycling of the co-factor dihydrofolic acid (DHF). Thymidylic acid (2-deoxy-thymidine monophosphate, dTMP) is an essential nucleotide precursor of DNA synthesis. It is produced by the enzyme thymidylate synthetase by transfer of a methyl group from tetrahydrofolic acid (THF) to the uracil base on uridylic acid (2-deoxyuridine monophosphate, dUMP) (Fig. 12.5). THF is converted to DHF in this process and must be reverted to THF by the enzyme dihydrofolate reductase (DHFR) before... 

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