35638-82-5

Upstream product

• 100-39-0 benzyl bromide 
• 58-61-7 adenosine 
• 100-46-9 benzylamine 
• 1576-37-0 N-benzyl-p-toluenesulfonamide 
• 33528-13-1 N-nitroso-N-benzyl-p-toluenesulphonamide 
• 17331-15-6 (E)-N'-(9-((2S,3R,4S,5R)3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-9H-purin-6-yl)-N,N-dimethylformimidamide 
• 908094-04-2 phenyldiazomethane 
• 228243-48-9 6-chloro-9-(3-O-benzoyl-β-D-ribofuranosyl)purine 
• 568584-95-2 9-(3-O-benzoyl-2-O-benzyl-β-D-ribofuranosyl)-6-chloropurine 
• 100-51-6 benzyl alcohol 

Downstream Products

• 58-61-7 adenosine 

Relevant academic research and scientific papers

A new method for the synthesis of 2′-O-benzyladenosine using mitsunobu reaction

A new method to introduce a benzyl group onto the 2′-OH of purine ribonucleoside is described. Thus, 6-chloropurine 3′-O-benzoylriboside and its 5′-O-trityl congener were condensed with benzyl alcohol using the Mitsunobu reaction to give the 2′-O-benzyl derivative. The yields were varied from 4.6 to 62.9% depending on the solvent used. The product was converted to adenosine, indicating that the stereochemistry at C-2′ is retained.

Structure-guided design of a methyl donor cofactor that controls a viral histone H3 lysine 27 methyltransferase activity

vSET (a viral SET domain protein) is an attractive polycomb repressive complex 2 (PRC2) surrogate to study the effect of histone H3 lysine 27 (H3K27) methylation on gene transcription, as both catalyze histone H3K27 trimethylation. To control the enzymatic activity of vSET in vivo with an engineered S-adenosyl-l-methionine (SAM) analogue as methyl donor cofactor, we have carried out structure-guided design, synthesis, and characterization of orthogonal vSET methyltransferase mutant/SAM analogue pairs using a "bump-and-hole" strategy.

Introduction of a benzyl group onto the 2′-OH of 6-chloropurine 3′-O-benzoylriboside

A new method to introduce a benzyl group onto the 2′-OH of purine ribonucleoside is described. Thus, 6-chloropurine 3′-O-benzoylriboside and its 5′-O-trityl congener were condensed with benzyl alcohol using the Mitsunobu reaction to give the 2′-O-benzyl derivative. The yields were varied from 4.6 to 62.9% depending on the solvent. The product was converted to adenosine, indicating that the stereochemistry at C-2′ is retained.

Protecting Groups in Nucleosides and Nucleotides Synthesis. VIII. Synthesis of (4-Substituted 2-Picolyl 1-Oxide)halides and 2'- and 3'-O-(4-Substituted-2-picolyl 1-Oxide)nucleosides

A number of alkylating agents of the 4-substituted pyridine N-oxide series, such as (4-nitro-, 4-methylthio-, or 4-methoxy-2-picolyl 1-oxide)halide, have been prepared.Treatment of 2',3'-O-(dibutylstannylene)uridine or 2',3'-O-(dibutylstannylene)adenosine with the alkylating agents afforded the corresponding 2'-O- and 3'-O-(4-substituted 2-picolyl 1-oxide)nucleosides. 2'-O-(4-Nitro-2-picolyl 1-oxide)uridine was converted to the 4-methoxy-2-picolyl derivative on treatment with methanolic sodium methoxide at 60 deg C.However, it was found that the treatment of adenosine with sodium hydride in DMF, followed by alkylation with (4-methoxy-2-picolyl 1-oxide)chloride gave a more satisfactory yield (56.4percent) of 2'-O-(4-methoxy-2-picolyl 1-oxide)adenosine. 2'-O-(4-Methylthio-2-picolyl 1-oxide)adenosine could be similarly prepared in 36.7percent yield. 4-Methoxy-2-picolyl protection was removable under milder conditions than 2-picolyl 1-oxide protection.Phosphorylation of 17 with phosphoryl chloride in triethyl phosphate gave the corresponding 5'-phosphate in 57.8percent yield.Keywords - 4-substituted 2-picolyl 1-oxide; protecting group in nucleotide synthesis; acetic anhydride rearrangement of α-picolyl 1-oxide; 2'-O-substituted adenosine; 2'-O-substituted uridine; 4-methoxy-2-pyridyl carbinol 1-oxide; 4-methylthio-2-pyridyl carbinol 1-oxide; 4-nitro-2-pyridyl carbinol 1-oxide.