52448-07-4

Upstream product

• 65-71-4 thymin 
• 99395-04-7 1-O-acetyl-2,3,5-tri-O-benzoyl-D-xylofuranose 
• 7288-28-0 2,4-bis(trimethylsiloxy)-5-methylpyrimidine 
• 20822-87-1 1-O-acetyl-2,3,5-tri-O-benzoyl-α-D-xylofuranose 
• 65-71-4 2,4-dihydroxy-5-methylpyrimidine 

Downstream Products

• 52486-19-8 1-(β-D-xylofuranosyl)-thymine 
• 68027-42-9 5-methyl-4-thioxo-1-(tri-O-benzoyl-β-D-xylofuranosyl)-3,4-dihydro-1H-pyrimidin-2-one 

Relevant academic research and scientific papers

Propargyl 1,2-orthoesters for a catalytic and stereoselective synthesis of pyrimidine nucleosides

Pyrimidine nucleosides are synthesized by using propargyl 1,2-orthoesters and Au(III) salt as a catalyst. Strategically positioned 1,2-orthoesters are found to yield only 1,2-trans nucleosides and enable preparation of 2′-OH containing pyrimidine nucleosides. The glycosyl donor employed in this study is stable and easily accessible. The identified high-yielding protocol is mild, diastereoselective, and catalytic.

A procedure for facile synthesis of nucleosides using N, O-Bistrimethyl- silylacetamide in the presence of natural phosphate coated with potassium iodide

Several α-D/L-arabino and β-D/L- xylonucleosides were synthesized in good yields under mild conditions by N-glycosylation of 1-O-acetyl D/L- arabino, and xylofuranose, with silylated nucleobases (uracil, thymine and 6- azauracil) in acetonitrile using natural phosphate (NP) coated with potassium iodide in BSA as catalyst.

Process for the deoxygenation of nucleosides

An efficient process for the deoxygenation of 2'- and or 3'-hydroxyl groups of a nucleoside that includes reacting the hydroxyl group with 3-halopropionitrile or 2-nitroethylhalide and carbon disulfide in base to form a 2'- or 3'-(cyanoethylthio or nitroethylthio)thiocarbonyl, that is reductively eliminated and replaced with hydrogen. The deoxygenation process can be used in a wide variety of nucleoside syntheses that require the elimination of the 2'- or 3'-hydroxyl groups, including the preparation of 3'-substituted-2',3'-dideoxynucleosides such as 3'-azido-3'-deoxythymidine and 3'-azido-2',3'-dideoxyuridine.

Process for the preparation of 3'-azido-3'-deoxythymidine and intermediates

This invention relates to a new synthetic process for the manufacture of zidovudine from the starting material D-xylose involving: i) Conversion of D-xylose to a 2′,3′,5′-protected derivative of 1-(β-D-xylofuranosyl)thymine; ii) 2′-Deoxygenation of the xylofuranosyl thymine; and iii) 3′-Azidation of the 2′-deoxy compound.

Systematic Synthesis and Biological Evaluation of α- and β-D-Xylofuranosyl Nucleosides of the Five Naturally Occurring Bases in Nucleic Acids and Related Analogues

The α- and β-D-xylofuranosyl analogues of the naturally occurring nucleosides, as well as other D-xylofuranosyl derivatives, have been the subject of a systematic synthesis and examination of their biological, i.e. antiviral antimetabolic, and cytostatic