65475-49-2Relevant academic research and scientific papers
Synthesis of bicyclic 2′-deoxynucleosides with α-L-ribo- And β-D-xylo-configurations and restricted S- and N-type conformations
Shaikh, Khalil I.,Kumar, Surender,Lundhus, Lene,Bond, Andrew D.,Sharma, Pawan K.,Nielsen, Poul
experimental part, p. 1557 - 1566 (2009/10/01)
Two bicyclic 2'′-deoxynucleoside analogues are synthesized in 12 steps each from thymidine. With a six- membered ring fused to the C3'′-C4'′ bond and an α-L-ribo- and a β-D-xylo- configuration, these are conformationally restricted in an S- and an N-type
NUCLEOSIDE ANALOGUES WHOSE SUGAR MOIETIES ARE BOUND IN S-FORM AND OLIGONUCLEOTIDE DERIVATIVES COMPRISING NUCLEOTIDE ANALOGUES THEREOF
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Page 27; 29, (2010/02/09)
Compounds of the following general formula (1) and salts thereof: where A represents an alkylene group having 1 to 2 carbon atoms, etc.; B represents an aromatic heterocyclic group which may have a substituent, etc.; R1 and R2 each represent a hydrogen atom, a protective group for a hydroxyl group for synthesis of nucleic acid, a phosphate group, or -P(R4)R5 [where R4 and R5 are the same or different, and each represent a hydroxyl group, a hydroxyl group protected with a protective group for synthesis of nucleic acid, a mercapto group, a mercapto group protected with a protective group for synthesis of nucleic acid, etc.]; and R3 represents a hydrogen atom, a halogen atom, a hydroxyl group, a hydroxyl group protected with a protective group for synthesis of nucleic acid, etc. These compounds are useful for producing oligonucleotide analogues useful for the antisense method, antigene method, etc., and for producing their intermediates.
Efficient synthesis of 2'-deoxynucleoside 3'-C-phosphonates: Reactivity of geminal hydroxyphosphonate moiety
Kralikova,Budesinsky,Masojidkova,Rosenberg
, p. 1159 - 1183 (2007/10/03)
In this report we present a novel, simple way for the synthesis of 3'-C-phosphonate derivatives of all four basic 2'-deoxynucleosides in both fully protected and deprotected forms. The reactivity of the geminal hydroxy phosphonate moiety located at the 3'
Mild Periodinane Oxidation of Protected Nucleosides to Give 2'- and 3'-Ketonucleosides. The First Isolation of a Purine 2'-Deoxy-3'-ketonucleoside Derivative
Samano, Vicente,Robins, Morris J.
, p. 5186 - 5188 (2007/10/02)
Oxidation of 3',5'- or 2',5'-bis-O-silyl-protected nucleosides with Dess-Martin 12-I-5 periodinane reagent, 1,1,1-tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3(1H)-one (I), in dichloromethane gives 2'- or 3'-ketonucleoside derivatives, respectively.Isolation of the first purine 2'-deoxy-3'-ketonucleoside derivative (2d) has been accomplished by periodinane oxidation of 5'-O-(tert-butyldiphenylsilyl)-2'-deoxyadenosine (1d).
SYNTHESIS OF 2',3'-DIDEOXY-3'-METHYLENE PYRIMIDINE NUCLEOSIDES AS POTENTIAL ANTI-AIDS AGENTS
Sharma, M.,Bobek, M.
, p. 5839 - 5842 (2007/10/02)
Efficient synthesis of 2',3'-dideoxy-3'-methylene nucleoside analogs starting from 2'-deoxy-3'-keto-nucleosides is described.
SYNTHESIS OF CHEMICALLY REACTIVE ANALOGUES OF AZT AND THEIR BIOLOGICAL EVALUATION AGAINST HIV
Schreiber, Stuart L.,Ikemoto, Norihiro
, p. 3211 - 3214 (2007/10/02)
Several 3'-deoxythymidine analogues were prepared and tested against HIV.The choice of analogues was based on their possible covalent binding to the enzyme reverse transcriptase.
2' AND 3'-KETONUCLEOSIDES AND THEIR ARABINO AND XYLO REDUCTION PRODUCTS CONVENIENT ACCESS VIA SELECTIVE PROTECTION AND OXIDATION OF RIBONUCLEOSIDES
Hansske, Fritz,Madej, Danuta,Robins, Morris J.
, p. 125 - 135 (2007/10/02)
A number of 2',5'- or 3',5'-diprotected ribonucleosides and 5'-protected 2'- or 3'-deoxy-β-D-erythro-pentofuranosyl nucleosides have been oxidized to the corresponding 3' or 2'-ketonucleoside derivatives using chromium trioxide/pyridine/acetic anhydride or dimethyl sulfoxide/acetic anhydride.Reduction of the carbonyl functions with sodium borohydride gave the inverted arabino, xylo, or deoxy-threo isomers as predominant products by attack at the less hindered α-face of the sugar ring.Parallel reductions using sodium borodeuteride corroborated the epimeric ratios by demonstrating that complete oxidation of the original hydroxyl groups had occured.The deuterium labeling also aided in making NMR spectral assignments.
NUCLEIC ACID RELATED COMPOUNDS. 43. A CONVENIENT PROCEDURE FOR THE SYNTHESIS OF 2' AND 3'-KETONUCLEOSIDES
Hansske, Fritz,Robins, Morris J.
, p. 1589 - 1592 (2007/10/02)
Chromium trioxide/pyridine/acetic anhydride effects smooth oxidation of selectively protected nucleosides to give high yields of 2' or 3'-ketonucleosides, whose reduction provides the inverted nucleoside epimers.
