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- W2092284672 abstract "Previously, we synthesized 4‘-thioFAC, a novel antineoplastic cytosine nucleoside, by developing an original method. However, several problems remained. To overcome these problems, we have developed an alternative method for the synthesis of 4‘-thionucleosides. In the original synthesis, carbons from C1 to C5 of d-glucose were used. The new method also starts from d-glucose but uses carbons closer to the tail (C2−C6). A dibenzoyl derivative obtained by this approach was brominated at the anomeric position to give a 1-bromide derivative. Fusion of the 1-bromide and persilylated acetylcytosine, followed by deprotection, predominantly gave a β-anomer of 4‘-thioFAC. The reaction of 2,6-diaminopurine with the 1-bromide in the presence of TMS triflate gave a glycosylated product in good yield. After deprotection, the resulting 1:1 anomeric mixture of free nucleosides was treated with adenosine deaminase to give a β-anomer of 4‘-thioFAG, a guanine congener of 4‘-thioFAC, selectively. Using a similar approach, we..." @default.
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- W2092284672 date "2010-06-11" @default.
- W2092284672 modified "2023-09-25" @default.
- W2092284672 title "ChemInform Abstract: An Alternative Synthesis of the Antineoplastic Nucleoside 4′-ThioFAC and Its Application to the Synthesis of 4′-ThioFAG and 4′-Thiocytarazid." @default.
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- W2092284672 doi "https://doi.org/10.1002/chin.200005253" @default.
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