213313-43-0

Upstream product

• 67-56-1 methanol 
• 131139-02-1 (3aS,5R,6R,6aS)-6-(benzyloxy)-5-((benzyloxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole 
• 114738-04-4 (3aS,5R,6R,6aS)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol 
• 168608-39-7 (3S,4S,5R)-5-(((tert-butyldiphenylsilyl)oxy)methyl)tetrahydrofuran-2,3,4-triol 
• 10323-20-3 D-Arabinose 
• 100-44-7 benzyl chloride 
• 817204-28-7 C₂₀H₂₂O₅ 
• 191543-71-2 methyl 3,5-di-O-benzyl-α-D-ribofuranoside 
• 37077-81-9 1,2-isopropylidene-α-D-ribofuranose 

Downstream Products

• 78246-87-4 (2R,3R,4R)-3-(benzyloxy)-2-((benzyloxy)methyl)-4-chloro-5-methoxytetrahydrofuran 
• 213313-44-1 methyl 3,5-di-O-benzyl-2-O-(p-toluenesulfonyl)-D-arabinofuranoside 
• 863642-46-0 (3R,4R,5R)-4-(benzyloxy)-5-(benzyloxymethyl)-3-fluorotetrahydrofuran-2-yl acetate 
• 863642-44-8 methyl 3,5-di-O-benzyl-2-deoxy-2-fluoro-α/β-D-ribofuranoside 
• 863642-77-7 ((2R,3R,4S,5R)-5-Allyl-3-benzyloxy-4-fluoro-tetrahydro-furan-2-yl)-methanol 

Relevant academic research and scientific papers

CYCLIC DINUCLEOTIDE COMPOUND AND USES THEREOF

Provided are a compound of formula (I), an optical isomer thereof, a pharmaceutically acceptable salt thereof, uses of said compound acting as a STING agonist.

CYCLIC DINUCLEOTIDES AS ANTICANCER AGENTS

The present invention is directed to compounds of the formulae I, II and III as shown below wherein all substituents are defined herein, as well as pharmaceutically acceptable compositions comprising compounds of the invention and methods of using said compositions in the treatment of various disorders.

NUCLEOTIDE AND NUCLEOSIDE 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.

Stereoselective C-glycosylation reactions of ribose derivatives: Electronic effects of five-membered ring oxocarbenium ions

The factors controlling the highly α-selective C-glycosylation of ribose derivatives were determined by examining the Stereoselective reactions of 18 ribose analogues differing in substitution at C-2, C-3, and C-4. The lowest energy conformers of the intermediate oxocarbenium ions display the C-3 alkoxy group in a pseudoaxial orientation to maximize electrostatic effects. To a lesser extent, the C-2 substituent prefers a pseudoequatorial position, and the alkyl group at C-4 has little influence on conformational preferences. In all cases, the product was formed by stereoelectronically preferred inside attack on the lowest energy conformer.

Syntheses and reactions of 5-O-acetyl-1,2-anhydro-3-O-benzyl-α-D-ribofuranose and -β-D-lyxofuranose, 5-O-acetyl-1,2-anhydro-3,6-di-O-benzyl- and 1,2-anhydro-5,6-di-O-benzoyl-3-O-benzyl-β-D-mannofuranose, and 6-O-acetyl-1,2-anhydro-3,4-di-O-benzyl-α-D-glucopyranose and -β-D-talopyranose

The title compounds 5-O-acetyl-1,2-anhydro-3-O-benzyl-α-D-ribofuranose and 5-O-acetyl-1,2-anhydro-3-O-benzyl-β-D-lyxofuranose, and 6-O-acetyl-1,2-anhydro-3,4-di-O-benzyl-α-D-glucopyranose and 6-O-acetyl-1,2-anhydro-3,4-di-O-benzyl-β-D-talopyranose, and 5-O-acetyl-1,2-anhydro-3,6-di-O-benzyl-β-D-mannofuranose and 1,2-anhydro-5,6-di-O-benzoyl-3-O-benzyl-β-D-mannofuranose have each been synthesized from the corresponding 2-O-tosylate and 1-free hydroxyl intermediates by base-initiated intramolecular SN2 ring closure in almost quantitative yields. Acetyl and benzoyl groups were not affected in the ring closure reactions. Condensation of 6-O-acetyl-1,2-anhydro-3,4-di-O-benzyl-α-D-glucopyranose and 5-O-acetyl-1,2-anhydro-3,6-di-O-benzyl-β-D-mannofuranose with 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose in the presence of ZnCl2 as the catalyst afforded the 1,2-trans-linked 6-O-acetyl-3,4-di-O-benzyl-β-D-glucopyranosyl-(1 → 6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose and 5-O-acetyl-3,6-di-O-benzyl-α-D-mannofuranosyl-(1 → 6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose as the sole products in satisfactory yields, while condensation of 5-O-acetyl-1,2-anhydro-3-O-benzyl-β-D-lyxofuranose with 3-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranose yielded the 1,2-trans-linked 5-O-acetyl-3-O-benzyl-α-D-lyxofuranosyl-(1 → 5)-3-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranose as the sole product in a good yield. The 6-O-acetyl group in the glycosyl donor, 6-O-acetyl-1,2-anhydro-3,4-di-O-benzyl-α-D-glucopyranose, did not influence the stereoselectivity of the ring-opening-coupling reaction.