212970-72-4

Upstream product

• 58479-61-1 tert-butylchlorodiphenylsilane 
• 63593-03-3 1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose 
• 22331-21-1 1,2:5,6-di-O-isopropylidene-3-O-benzyl-α-D-allofuranose 
• 57099-04-4 3-O-benzyl-1,2-O-isopropylidene-α-D-allofuranose 
• 63593-02-2 3-O-benzyl-1,2-O-isopropylidene-α-D-ribo-pentodialdo-1,4-furanose 

Downstream Products

• 212970-73-5 3-O-benzyl-5-O-tert-butyldiphenylsilyl-1,2-O-isopropylidene-4-C-(p-toluenesulfonyl)oxymethyl-α-D-erythro-pentofuranose 
• 473290-44-7 1-({(1S,3R,4S,5R)-7,7-dimethyl-2,6,8-trioxa-4-(phenylmethoxy)-3-[(phenylmethoxy)methyl]-bicyclo[3.3.0]oct-3-yl}methoxy)-2,2-dimethyl-1,1-diphenyl-1-silapropane 
• 454715-80-1 5-O-(tert-butyldiphenylsilyl)-3-O-benzyl-4-C-formyl-1,2-O-isopropylidene-α-D-erythropentofuranose 
• 851345-97-6 3-O-benzyl-5-O-tert-butyldiphenylsilyl-4-C-ethoxymethylene-1,2-isopropylidene-β-D-ribo-pentofuranose 
• 860651-67-8 ((3aR,5R,6S,6aR)-6-Benzyloxy-5-iodomethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethoxy)-tert-butyl-diphenyl-silane 
• 583829-86-1 4-C-acetoxymethyl-1,2-di-O-acetyl-3-O-benzyl-5-O-tert-butyldiphenylsilyl-D-erythro-pentofuranose 
• 583829-91-8 4-N-benzoyl-2'-O,4'-C-(methylenoxymethylene)cytidine 
• 519056-24-7 3'-O-benzyl-5-methyl-2'-O,4'-C-(methylenoxymethylene)uridine 
• 877823-51-3 4-N-benzoyl-5-methyl-2'-O,4'-C-(methylenoxymethylene)cytidine 
• 583829-90-7 4-N-benzoyl-3'-O-benzyl-2'-O,4'-C-(methylenoxymethylene)cytidine 
• 877823-50-2 4-N-benzoyl-3'-O-benzyl-5-methyl-2'-O,4'-C-(methylenoxymethylene)cytidine 
• 519056-26-9 5'-O-(4,4'-dimethoxytrityl)-5-methyl-2'-O,4'-C-(methylenoxymethylene)uridine 
• 519056-22-5 3'-O-benzyl-5'-O-tert-butyldiphenylsilyl-4'-C-hydroxymethyl-5-methyluridine 
• 519056-23-6 3'-O-benzyl-5'-O-tert-butyldiphenylsilyl-5-methyl-2'-O,4'-C-(methylenoxymethylene)uridine 

Relevant academic research and scientific papers

Conformationally constrained analogues of diacylglycerol (DAG). Part 19: Asymmetric syntheses of (3R)- and (3S)-3-hydroxy-4,4-disubstituted heptono-1,4-lactones as protein kinase C (PK-C) ligands with increased hydrophilicity

The stereospecific introduction of (R)- and (S)-OH groups at position C-3 of two diacylglycerol γ-lactones (DAG-lactones) previously identified as strong protein kinase C (PK-C) ligands is presented. The compounds were designed to investigate whether the extra OH group in a specific orientation could establish an additional hydrogen bond with the C1 domain of PK-C, thus providing a DAG analogue with reduced lipophilicity. The OH groups were introduced following two different diastereoselective multistep syntheses starting from diacetone-D-glucose. The PK-C binding affinities for the new compounds were weaker in comparison to those of the parent compounds, suggesting that the extra OH does not engage efficiently in hydrogen bonding at the receptor.

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