188413-96-9

Upstream product

• 66-22-8 uracil 
• 199446-50-9 C₃₈H₃₄O₉Si 
• 22224-41-5 1,3,5-tri-O-benzoyl-α-D-ribofuranoside 
• 1066-54-2 trimethylsilylacetylene 
• 188413-88-9 1,3,5-tri-O-benzoyl-2-C-[(trimethylsilyl)ethynyl]-α-D-ribofuranose 
• 157037-56-4 1,3,5-tri-O-benzoyl-2-oxo-α-D-erythro-pentofuranose 
• 98-88-4 benzoyl chloride 
• 188413-93-6 1,2,3,5-tetra-O-benzoyl-2-C-trimethylsilylethynyl-β-D-ribofuranose 

Downstream Products

• 188413-98-1 1-((2R,3R,4R,5R)-3-ethynyl-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione 

Relevant academic research and scientific papers

ALKYNE CONTAINING NUCLEOTIDE AND NUCLEOSIDE THERAPEUTIC COMPOSITIONS AND USES RELATED THERETO

This disclosure relates to nucleotide and nucleoside therapeutic compositions and uses in treating infectious diseases, viral infections, and cancer, where the base of the nucleotide or nucleoside contains at least one thiol, thione or thioether.

A short, flexible route toward 2'-C-branched ribonucleosides

A five-step synthesis of 2'-C-branched ribonucleosides from commercially obtained 1,3,5-tri-O-benzoyl-α-D-ribofuranose (4) is described. The free hydroxyl group of 4 was oxidized in high yield with Dess-Martin periodane reagent. The resultant 2-ketosugar was treated with MeMgBr/TiCl4, CH2=CHMgBr/CeCl3, or TMSC≡CLi/CeCl3, and in each case addition to the ketone proceeded stereoselectively to provide 2-alkylated ribofuranosides. After conversion to the corresponding tetrabenzoyl derivatives, the 2-alkylribofuranosides were coupled to nucleobases under Vorbruggen persilylation conditions, giving the β-nucleosides with high stereoselectivity. Deprotection with methanolic ammonia provided the title compounds in 17-49% overall yields from 4.