134953-47-2Relevant academic research and scientific papers
Efficient electrochemical N-glycosylation of silylated pyrimidines with protected arylthioriboses in the presence of a catalytic amount of NBS or Br2
Nokami, Junzo,Osafune, Masahiro,Ito, Yuichiro,Miyake, Fumiaki,Sumida, Shin-Ichi,Torii, Sigeru
, p. 1053 - 1054 (2007/10/03)
Electrolysis of silylated pyrimidines with protected arylthioribose, in the presence of a catalytic amount of NBS or Br2 as a mediator in an undivided cell, gave the corresponding N-glycosides (nucleosides) in good yield.
RADICAL DEOXYGENATION OF DINUCLEOSIDE THIOCARBONATES
Antonov, K. V.,Karpeiskii, A. M.,Miroshnikov, A. I.
, p. 236 - 240 (2007/10/02)
The synthesis of a series of dinucleoside thiocarbonates has been described and the possibility has been shown of their use as substrates for the radical deoxygenation reaction.A new method is proposed for the synthesis of dideoxy- and 2'-deoxynucleosides
Stereoselective Synthesis of 2'-Deoxy-β-D-threo-pentofuranosyl Nucleosides by the NBS-Promoted Coupling Reaction of Thioglycosides with Silylated Heterocyclic Bases
Sugimura, Hideyuki,Osumi, Kenji,Kodaka, Yasuko,Sujino, Keiko
, p. 7653 - 7660 (2007/10/02)
The NBS-promoted coupling reaction of phenyl 3,5-O-isopropylidene-2-deoxy-1-thio-α-D-threo-pentofuranoside (5e) with silylated pyrimidine bases was found to proceed in a highly stereoselective manner (α:β = 1:24 - 0:1) to afford 2'-deoxy-β-D-threo-pentofuranosyl pyrimidine nucleosides in satisfactory yields.The highly stereoselective outcome is thought to result from an in situ anomerization-type mechanism, in which intimate ionic intermediates would be in equilibrium and anomerize to the sterically preferable α form.A subsequent SN2 type attack to the intermediate will lead to the β-nucleosides.By using this method, the synthesis of L-nucleosides, 1-(2-deoxy-β-L-threo-pentofuranosyl)thymine and cytosine derivatives, was also demonstrated by starting from the L-enantiomer of the thioglycoside.On the other hand, the reaction with purine bases was accompanied by the production of undesirable N-7 regioisomers besides the desired N-9 products.The product distribution of the regioisomers was, however, proved to change with reaction time.For instance, a long reaction period allowed the thermodynamically stable N-9 isomers to be exclusively produced with moderate selectivity (α:β = 1:2 - 1:4.8).The isolated yields to the 9-β isomers after purification were acceptable for practical use.
β-Selective synthesis of 2′-deoxynucleosides by the coupling of 2-deoxy-1-thio-D-threo-pentofuranosides with silylated thymine
Sugimura, Hideyuki,Sujino, Keiko,Osumi, Kenji
, p. 2515 - 2516 (2007/10/02)
The coupling of the 3,5-O-isopropylidene derivative of phenyl 2-deoxy-1-thio-D-threo-pentofuranoside with silylated thymine in the presence of N-bromosuccinimide yielded 1-(2-deoxy-β-D-threo-pentofuranosyl)thymine with highly anomeric selectivity.
Preparation of 3'-azido-3'-deoxy-thymidine (AZT) from D-xylose.
Benhaddou, R.,Czernecki, S.,Valery, J. M.,Bellosta, V.
, p. 108 - 111 (2007/10/02)
A synthetic route to 3'-azido-3'-deoxy-thymidine (AZT) starting from readily available D-xylose is described.In order to perform complete stereocontrol during the coupling step we decided to prepare the D-xylofuranose synthon 6a bearing a participating group at C-2 and non base-labile protective groups at C-3 and C-5.Thus, further selective deprotection at C-2' of the resulting nucleoside, followed by deoxygenation is straightforward and affords (2'-deoxy-β-D-threo-pentofuranosyl)-thymine 11, a precursor close to AZT.
Stereoselective Synthesis of β-2-Deoxyribonucleosides from 1-O-Acetyl-3-O--2-deoxyribose
Okauchi, Tatsuo,Kubota, Hideki,Narasaka, Koichi
, p. 801 - 804 (2007/10/02)
β-2-Deoxyribonucleosides are prepared stereoselectively from 1-O-acetyl-5-O-benzyl-3-O--2-deoxy-D-erythro-pentofuranose by the reaction with the silyl or zinc derivatives of nucleoside bases in the presence of trimethylsilyl trifl
STEREOCHEMICAL CONTROL AS A FUNCTION OF PROTECTING-GROUP PARTICIPATION IN 2-DEOXY-D-ERYTHRO-PENTOFURANOSYL NUCLEOSIDES
Wierenga, Wendell,Skulnick, Harvey I.
, p. 41 - 52 (2007/10/02)
Possible features controlling the anomeric ratios in the synthesis of the antiviral antibiotic dihydro-5-azathymidine have been examined.Replacement of the 3- and 5-(4-methylbenzoyl) protecting groups in 2-deoxy-D-erythro-pentofuranosyl chloride by benzyl
