36792-96-8Relevant academic research and scientific papers
Synthesis of triazol Cn-ribonucleoside phosphoramidites using β-ribofuranosyl-cn-acetylenes for RNA catalysis probing
Yoneyama, Hiroki,Hikasa, Fumiko,Fujisue, Daiki,Usami, Yoshihide,Zhao, Zheng-Yun,Harusawa, Shinya
, p. 106 - 126 (2018/01/26)
Novel C4-linked triazol C0-, C1- and C2-ribonucleoside phosphoramidites for RNA catalysis probing were synthesized from β-ribofuranosyl-Cn-acetylenes (n = 0–2), which were efficiently prepared by fragmentation of tetrazoles derived from cyanophosphates. N
Synthesis of C -Ribosyl-1,2,3-triazolyl Carboxamides
Solarte, Carmen,Dos Santos, Micha?l,Gonzalez, Simon,Miranda, Leandro S. M.,Guillot, Régis,Ferry, Angélique,Gallier, Florian,Uziel, Jacques,Lubin-Germain, Nadège
, p. 1993 - 2002 (2017/04/26)
Because of the emergence of new viruses, the need for new antiviral broad-spectrum compounds remains important. In this context, herein the synthesis of C-nucleosides, structurally close to ribavirin, a nucleoside presenting various biological activities and used until now particularly for its broad-spectrum antiviral properties, is reported. The compounds were designed in order to increase their stability and the number of hydrogen bond donor or acceptor in comparison to ribavirin, and to investigate the role of the carboxamide group on the biological activity. The efficient synthesis of 11 C-nucleosides is based on an indium-mediated alkynylglycosylation as the key step, followed by the construction of the triazole heterocycle. Amidation was performed with primary and secondary amines in yields up to 85%. An analogue nucleoside with a triazole without carboxamide group was also prepared in order to compare its activity. Finally, the carboxamide group was moved to the N-1 triazole position to mimic ribavirin.
Transformation of Carbonyl Compounds into Homologous Alkynes under Neutral Conditions: Fragmentation of Tetrazoles Derived from Cyanophosphates
Yoneyama, Hiroki,Numata, Masahiro,Uemura, Kenji,Usami, Yoshihide,Harusawa, Shinya
, p. 5538 - 5556 (2017/06/07)
Cyanophosphates (CPs) can be easily prepared from either ketones or aldehydes, and their reaction with NaN3-Et3N·HCl results in the formation of azidotetrazoles. Under microwave irradiation, successive fragmentation of the azidotetrazoles generates alkylidene carbenes that undergo [1,2]-rearrangement and are transformed into homologous alkynes. Treatment of ketone-derived CPs with TMSN3 and Bu2SnO as catalyst in toluene at reflux directly yields the corresponding internal alkynes, whereas the reaction of aldehyde-derived CPs with NaN3-Et3N·HCl in THF at reflux or TMSN3-Bu2SnO (cat.) in toluene at reflux provides homologous terminal alkynes in good yields. These reactions take place under neutral conditions and can be successfully extended to obtain alkynes that are not usually accessible from the corresponding carbonyl compounds by the Ohira-Bestmann or Shioiri procedures, which require basic conditions.
C-Nucleoside Studies. Part 13. A New Synthesis of 2,3,5-Tri-O-benzyl-α(and β)-D-ribofuranosylethyne Involving Benzyloxy Participation, and a Synthesis of α-Showdomycin
Aslani-Shotorbani, Gaffar,Buchanan, J. Grant,Edgar, Alan R.,Shanks, Colin T.,Williams, Gavin C.
, p. 2267 - 2272 (2007/10/02)
2,3,4,6-Tetra-O-benzyl-D-glucitol (5) reacts with toluene-p-sulphonyl chloride in pyridine at 60 deg C to form mainly the furanoid products 2,3,6-tri-O-benzyl-1,4-anhydro-D-glucitol (10) and its 5-toluene-p-sulphonate (11) with loss of the 4-O-benzyl group.The pyranoid product tetra-O-benzyl-1,5-anhydro-D-glucitol preponderates when the intermediate 2,3,4,6-tetra-O-benzyl-1-O-toluene-p-sulphonyl-D-glucitol (6) is converted into its O-5 oxyanion.Benzyloxy participation has been exploited in a new synthesis of 2,3,5-tri-O-benzyl-α (and β)-D-ribofuranosylethyne, (20) and (4), from 2,3,4,5-tetra-O-benzyl-aldehydo-D-ribose.A synthesis of 2-α-D-ribofuranosylmaleimide, the α-isomer showdomycin, from (20) is described.
