118174-05-3Relevant academic research and scientific papers
Efficient and selective synthesis of glycofuranosyl azides and nucleosides from cyclic 1,2-thiocarbonate sugars
Alvarez De Cienfuegos, Luis,Rodriguez, Concepcion,Mota, Antonio J.,Robles, Rafael
, p. 2743 - 2745 (2003)
(Matrix presented) Cyclic 1,2-thiocarbonate sugars are convenient starting materials for the selective and efficient preparation of glycofuranosyl azides and nucleosides by regio- and stereoselective thiocarbonate ring-opening.
Highly β-stereoselective nucleosidation from α-D-xylo- and α-D-ribo-furanose 1,2-thiocarbonates
Robles, Rafael,Rodriguez, Concepcion,Alvarez De Cienfuegos, Luis,Mota, Antonio J.
, p. 831 - 838 (2007/10/03)
Cyclic 1,2-thiocarbonates of α-D-xylo- and α-D-ribo-furanoses were found to be excellent glycosyl donors in mild NIS-mediated nucleophilic substitution reactions, affording β-nucleosides with complete stereoselectivity and moderate to high yields after treatment with persilylated pyrimidinic bases. The nucleophile is believed to open the thiocarbonate ring at the anomeric position presumably via an SN2 mechanism. Participation of the nucleobase silylating agent [N,O-bis(trimethylsilyl) acetamide] in the mechanism of the nucleosidation step was shown, where a large excess of it has been proven to be necessary in order to achieve high yields. Absolute configurations at C-1′ were ascertained by chemical correlation synthesizing the corresponding 2,2′-anhydro-nucleosides.
SYNTHESE DE NUCLEOSIDES PYRIMIDIQUES NON PROTEGES EN O-2'A PARTIR DE SULFITES CYCLIQUES EN C-1-C-2
Gagnieu, Christian H.,Guiller, Alain,Pacheco, Henri
, p. 233 - 242 (2007/10/02)
Treatment of 3,5,6-tri-O-benzoyl-α-D-glucofuranose 1,2-sulfite with an excess of bis(trimethylsilyl) uracil, in fusion processes without any catalyst, afforded an excellent yield of 1-(3,5,6-tri-O-benzoyl-2-O-trimethylsilyl-β-D-glucopyranosyl)uracil, which was readily hydrolyzed in slightly acid conditions to give in almost quantitative yield 1-(3,5,6-tri-O-benzoyl-β-D-glucofuranosyl)uracil.This new synthetic method for nucleosides unprotected at O-2' was also tested in other sugar series.In some cases, only the 1',2'-trans-nucleosides were obtained, but in others, small yields (3-10percent) of 1',2'-cis-nucleosides were detected.The α-to-β ratio seems to be dependent on the reaction temperature. 2,4-Dimethoxypyrimidine also reacted with sugar 1,2-sulfites and 4-O-methyl-1-(3,5,6-tri-O-benzyl-β-D-glucopyranosyl)-2-pyrimidinone was prepared in 85percent yield from 3,5,6-tri-O-benzyl-α-D-glucopyranose 1,2-sulfite.
