199787-15-0Relevant academic research and scientific papers
Second-generation synthesis of protected phosphonothiodifluoromethylene analogues of nucleoside-3′-phosphates
Kalinina, Irina,Gautier, Arnaud,Salcedo, Carmen,Valnot, Jean-Yves,Piettre, Serge R.
, p. 4895 - 4900 (2007/10/03)
A practical, eight-step synthesis of the key intermediate 14 in 19% overall yield from α-D-xylose is described. The preparation can be carried out on multi-gram scale and involves the use of the organomagnesium reagent 2d. The capability of derivative 14 to be transformed into the title compounds is examplified by the preparation of 15. Additionally, X-ray crystallography of intermediate 12 provided the first structural data on difluorophosphonothioates.
Nucleosides and nucleotides. Part 212: Practical large-scale synthesis of 1-(3-C-ethynyl-β-D-ribo-pentofuranosyl)cytosine (ECyd), a potent antitumor nucleoside. Isobutyryloxy group as an efficient anomeric leaving group in the Vorbrüggen glycosylation reaction
Nomura, Makoto,Sato, Tsutomu,Washinosu, Masato,Tanaka, Motoaki,Asao, Tetsuji,Shuto, Satoshi,Matsuda, Akira
, p. 1279 - 1288 (2007/10/03)
A practical synthetic route to the antitumor nucleoside, 1-(3-C-ethynyl-β-D-ribo-pentofuranosyl)cytosine (ECyd, 1) from 1,2-O-isopropylidene-D-xylofuranose (3) has been developed. Since most of the compounds were obtained as crystals, the target ECyd was prepared without any chromatographic purification in 31% overall yield from compound 3. The isobutyryloxy group was found to be an effective leaving group at the anomeric position of the 3-β-C-ethynyl glycosyl donors in the key Vorbru?ggen glycosylation reaction. Using a similar procedure without chromatographic purification, the uracil congener EUrd [1-(3-C-ethynyl-β-D-ribo-pentofuranosyl)uracil (2), which also has a potent antitumor effect, was synthesized from 3 in 39% overall yield.
