3094-09-5Relevant articles and documents
Uracil nucleoside derivative and method for preparing deoxyuridine drug by using same (by machine translation)
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Paragraph 0068-0072, (2020/05/14)
The invention discloses (I) deoxy - D D-furan ribose 5 - styryl 1 - [2 - (1 - benzoate) derivative represented by the formula] and a preparation method, of the derivative, wherein the structure of the general formula (I) is shown. And the preparation method (I) of, deoxy - D D-furan ribose 5 - styryl 1 - [2 - (1 - benzoate) derivatives as above reaction raw materials can be used as a glycosyl donor to activate] under the conditions of the catalytic amount of the Lewis acid trifluoromethanesulfonate and N - iodosuccinimide, and, reaction efficient, yield 98%. reaching, is avoided in the conventional reaction system using an equivalent or excess of a Lewis acid, benzoyldiimide as a glycosyl donor. (by machine translation)
Synthesis of Nucleosides through Direct Glycosylation of Nucleobases with 5-O-Monoprotected or 5-Modified Ribose: Improved Protocol, Scope, and Mechanism
Downey, A. Michael,Pohl, Radek,Roithová, Jana,Hocek, Michal
supporting information, p. 3910 - 3917 (2017/03/27)
Simplifying access to synthetic nucleosides is of interest due to their widespread use as biochemical or anticancer and antiviral agents. Herein, a direct stereoselective method to access an expansive range of both natural and synthetic nucleosides up to a gram scale, through direct glycosylation of nucleobases with 5-O-tritylribose and other C5-modified ribose derivatives, is discussed in detail. The reaction proceeds through nucleophilic epoxide ring opening of an in situ formed 1,2-anhydrosugar (termed “anhydrose”) under modified Mitsunobu reaction conditions. The scope of the reaction in the synthesis of diverse nucleosides and other 1-substituted riboside derivatives is described. In addition, a mechanistic insight into the formation of this key glycosyl donor intermediate is provided.
A versatile synthesis of 5'-fenctionalized nucleosides through regioselective enzymatic hydrolysis of their peracetylated precursors
Bavaro, Teodora,Rocchietti, Silvia,Ubiali,Filice, Marco,Terreni, Marco,Pregnolato, Massimo
experimental part, p. 1967 - 1975 (2009/09/08)
We describe a chemo-enzymatic synthesis of modified nucleosides through lipase-catalyzed hydrolysis of their peracetylated precursors. It was found from screening of a large number of substrates that these enzymesregioselectivities were affected by the sugar and the nucleobase structures. By selecting the best enzyme for each substrate in terms of activity and regioselectivity, we prepared a small library of differently monodeprotecled purine and pyrimidine nucleosides useful as intermediates for the synthesis of high-value nucleosides and mononucleotides. By this approach, the chemo-enzymatic preparation of doxifluridine (14) and uridine 5'-monophosphate (5'-UMP, 15) from peracetylated uridine 1 was carried out. Elimination of many of the processing stages associated with existing methods was achieved, and higher yields and products of increased purity were generated. Wiley-VCH Verlag GmbH & Co. KGaA.
