134953-48-3Relevant academic research and scientific papers
Synthesis of purine nucleosides from D -glucuronic acid derivatives and evaluation of their cholinesterase-inhibitory activities
Xavier, Nuno M.,Schwarz, Stefan,Vaz, Pedro D.,Csuk, Rene,Rauter, Amelia P.
, p. 2770 - 2779 (2014/05/06)
Glucuronolactones were used as precursors for N9 and N 7 purine nucleosides containing glucuronic acid derivatives in their structures. Acetylated N-benzylglucofuran- and glucopyranuronamides were synthesized in a few steps from glucofuranurono-6,3-lactone. They were converted into the corresponding furanosyl and pyranosyl uronamide-based nucleosides by N-glycosylation with silylated 2-acetamido-6-chloropurine in the presence of trimethylsilyl triflate. The triacetylated bicyclic lactone was coupled itself with the nucleobase to give bicyclic N9,N7 nucleosides. Tri-O-acetylglucopyranurono-6,1-lactone was used for the first time as a glycosyl donor for N-glycosylation, and led to β-configured N9- and N7-linked purinylglucuronides under reaction conditions similar to those used with the 1-O-acetyl-substituted glycosyl donors. The cholinesterase inhibitory profiles of the synthetic nucleosides bearing glucuronic acid derivatives as glycons were evaluated, and they showed moderate selective acetylcholinesterase inhibitory activities (Ki = 14.78-50.53 μM). The best inhibition was shown by the furanosyl N 9-linked uronamide-based purine nucleoside. The synthesis of furanosyl and pyranosyl N9 and N7 purine nucleosides containing glucofuranurono-6,3-lactone, N-benzylglucuronamide, and glucuronic acid moieties is reported. Glucuronolactones were used as glycosyl donors or converted into suitable 1-O-acetyl derivatives for purine glycosylation. Some nucleosides showed moderate and selective inhibition of acetylcholinesterase. Copyright
Synthesis and glycosidic reaction of 1,2-anhydromanno-, lyxo-, gluco-, and xylofuranose perbenzyl ethers
Du, Yuguo,Kong, Fanzuo
, p. 797 - 817 (2007/10/03)
Stereospecific synthesis of 1,2-anhydromanno-, lyxo-, gluco-, and xylofuranose perbenzyl ethers was successfully achieved via intramolecular SN2 reaction of the corresponding C-1 alkoxide with C-2 bearing tosyloxy group. The key intermediates, furanose 2-sulfonates, were prepared from the corresponding 1,2-diols and tosyl chloride under phase transfer conditions in good yields. Condensation of the anhydro sugars with 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose or N-benzyloxycarbonyl L-serine methyl ester in the absence of catalyst gave 1,2-trans-linked glycofuranosides in high yield.
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.
