446862-77-7

Upstream product

• 64339-87-3 N₄,O-bis(trimethylsilyl)-N₄-benzoylcytosine 
• 260269-28-1 Acetic acid (2S,3S,4R)-4,5-diacetoxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-furan-3-yl ester 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 212970-74-6 Acetic acid (3R,4S,5S)-2-acetoxy-4-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-5-(toluene-4-sulfonyloxymethyl)-tetrahydro-furan-3-yl ester 
• 98-59-9 p-toluenesulfonyl chloride 
• 212970-72-4 {3-[(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)methyl]-(1S,3R,4S,5R)-7,7-dimethyl-2,6,8-trioxa-4-(phenylmethoxy)bicyclo[3.3.0]oct-3-yl}methan-1-ol 
• 63593-03-3 1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose 
• 446862-76-6 5-O-tert-butyldiphenylsilyl-4-C-(p-toluenesulfonyl)oxymethyl-1,2,3-tri-O-acetyl-β-D-erythro-pentofuranose 
• 212970-73-5 3-O-benzyl-5-O-tert-butyldiphenylsilyl-1,2-O-isopropylidene-4-C-(p-toluenesulfonyl)oxymethyl-α-D-erythro-pentofuranose 

Downstream Products

• 260269-38-3 N⁴-benzoyl-5'-O-tert-butyldiphenylsilyl-3'-O,4'-C-methylenecytidine 
• 446862-78-8 N⁴-benzoyl-5'-O-tert-butyldiphenylsilyl-4'-C-(p-toluenesulfonyl)oxymethylcytidine 

Relevant academic research and scientific papers

Synthesis and conformation of 3′,4′-BNA monomers, 3′-O,4′-C-methyleneribonucleosides

In order to develop novel 2′,5′-linked oligonucleotide analogues aimed for antivirus reagents and antisense/antigene oligonucleotides, novel nucleoside analogues, 3′-O,4′-C-methyleneribonucleosides (3′,4′-BNA monomers) were synthesized via two synthetic routes. The first route starting from uridine utilized a regioselective ring-closure reaction of the 4′-C-(p-toluenesulfonyl)oxymethyluridine derivative. The second route involved a coupling reaction of 1,2,3-tri-O-acetyl-4-C-(p-toluenesulfonyl)oxymethylribofuranose derivative with nucleobases followed by oxetan-ring formation to afford the 3′,4′-BNA monomers bearing all four nucleobases. By means of 1H NMR, X-ray crystallography and computational analysis, the sugar puckering of the 3′,4′-BNA monomers was found to be restricted in S-conformation (C1′-exo-C2′-endo puckering mode).

Facile synthesis and conformation of 3'-O,4'-C-methyleneribonucleosides

Bicyclic nucleoside analogues, 3'-O,4'-C-methyleneribonucleosides 1, including thymine, cytosine, adenine and guanine nucleobases, were conveniently synthesized from D-glucose, and the ribofuranose ring of I was found to exist predominantly in a S-conform