Regio- and stereoselective syntheses of l-pentose derivatives from l-arabinose

Add time:08/24/2019    Source:sciencedirect.com

Novel l-arabinose, l-ribose, 2-deoxy-l-ribose and 2-fluoro-2-deoxy-l-arabinose derivatives were synthesized from readily available l-arabinose. Different synthetic routes to methyl 3,5-di-O-acylated-l-arabino(ribo)furanosides as valued intermediates for the preparation of C-2 functionalized l-pentoses were investigated via regioselective transformations of 1,2-di-O-acetyl-3,5-di-O-pivaloyl-l-arabinofuranose, and selective acylation of methyl l-arabinofuranoside with 4-chlorobenzoyl or pivaloyl chloride. Short three-five-step syntheses of methyl 2-deoxy-α-l-ribofuranoside, its 3,5-di-O-acyl derivatives, valuable precursors for preparation of antiviral 2′-deoxy-l-nucleosides, were accomplished via simple and efficient reduction of methyl 2-O-mesyl-l-arabinofuranoside with L-Selectride or tandem reaction involving a complex hydride 2-deoxygenation/acylation of intermediate 2-deoxysugar. A new synthesis of 2′-deoxy-2′-fluoro-β-l-arabinofuranosyl thymine (l-FMAU) was performed using a mild fluorination of protected l-ribofuranoside and a novel sequence of conversions for the preparation of 2-deoxy-2-fluoro-l-arabinofuranoside derivatives.

We also recommend Trading Suppliers and Manufacturers of 2-Deoxy-alpha-L-erythro-pentofuranose (cas 113890-35-0). Pls Click Website Link as below: cas 113890-35-0 suppliers

Prev:The impact of Catechol-O-methyl transferase knockdown on the cell proliferation of hormone-responsive cancers
Next:Note1,2-Di-O-acetyl-5-O-benzoyl-3-deoxy-l-erythro-pentofuranose, a convenient precursor for the stereospecific synthesis of nucleoside analogues with the unnatural β-l-configuration)