197647-17-9Relevant academic research and scientific papers
An Alternative Synthesis of the Antineoplastic Nucleoside 4′-ThioFAC and Its Application to the Synthesis of 4′-ThioFAG and 4′-Thiocytarazid
Yoshimura, Yuichi,Endo, Mikari,Miura, Shinji,Sakata, Shinji
, p. 7912 - 7920 (1999)
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 synthesized 4′-thiocytarazid, which was not possible using the original method.
SYNTHETIC INTERMEDIATE OF 1-(2-DEOXY-2-FLUORO-4-THIO-?-D-ARABINOFURANOSYL)CYTOSINE, SYNTHETIC INTERMEDIATE OF THIONUCLEOSIDE, AND METHOD FOR PRODUCING THE SAME
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, (2015/06/10)
A compound represented by a formula [1D] as shown below (wherein R1A, R1B, R2A, R2B, R3A and R3B represent a hydrogen atom, an optionally substituted C1-6 alkyl group, and the li
