15397-13-4

Upstream product

• 69504-04-7 5'-O-(monomethoxytrityl)-2'-O-<(tert-butyl)dimethylsilyl>adenosine 
• 69504-05-8 3'-O-<(tert-butyl)dimethylsilyl>-5'-O-(monomethoxytrityl)adenosine 
• 58-61-7 adenosine 
• 51600-11-4 5'-O-(p-methoxyphenyldiphenylmethyl)adenosine 
• 125682-11-3 (2R,3R,4R,5R)-5-(6-Amino-purin-9-yl)-2-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-3-methyl-tetrahydro-furan-3,4-diol 
• 80541-14-6 3-O-acetyl-5-O-benzoyl-1,2-O-isopropylidene-3-C-methyl-α-D-ribofuranose 
• 125682-06-6 9-<5'-O-(4-monomethoxytrityl)-2'-O-t-butyldimethylsilyl-β-D-erythro-pentofuran-3'-ulosyl>adenine 
• 115236-92-5 9-(2,3-di-O-acetyl-5-O-benzoyl-3-C-methyl-β-D-ribofuranosyl)-N⁶-benzoyladenine 
• 125682-07-7 9-<2'-O-t-butyldimethylsilyl-3'-C-methyl-5'-O-monomethoxytrityl-β-D-xylofuranosyl>adenine 
• 4005-49-6 N-benzoyladenine 
• 125682-08-8 9-<2'-O-t-butyldimethylsilyl-3'-C-methyl-5'-O-monomethoxytrityl-β-D-ribofuranosyl>adenine 

Relevant academic research and scientific papers

Synthesis and Conformation of 9-(3'-C-Methyl-β-D-xylo-furanosyl)adenin and 3-C'-Methyladenosine, Two Sugar-Methylated Nucleoside Analogues

A novel synthetic route for the sugar-methylated nucleoside analogue 9-(3-C'-methyl-β-D-xylo-furanosyl)adenine (1) is reported.A Grignard reaction in THF with an appropriately protected keto nucleoside gave the xylo structure 4 in 60percent yield.Using diethyl ether as the solvent, the Grignard reaction furnished compound 4 in 35percent yield, along with the ribo epimer (ca. 1percent).The ribo epimer is the precursor of 3'-C-methyladenosine (2).Compounds 4 and 5 could be conveniently deprotected to obtain the title compounds in good yields.The conformational properties of 1 and 2 were analyzed using 500 MHz 1H NMR spectroscopy.In line with earlier experiments, it is found that the methyl group on the sugar ring strongly prefers an equatorial location.For 1, this results in the predominant population of the North (3T2) puckered form of the sugar ring, whereas compound 2 resides primarily in the South (2T3) conformation.

EPIMERIZATION DURING THE ACETOLYSIS OF 3-O-ACETYL-5-O-BENZOYL-1,2-O-ISOPROPYLIDENE-3-C-METHYL-α-D-RIBOFURANOSE. SYNTHESIS OF 3'-C-METHYLNUCLEOSIDES WITH THE β-D-ribo- AND α-D-arabino CONFIGURATIONS

Acetolysis of 3-O-acetyl-5-O-benzoyl-1,2-O-isopropylidene-3-C-methyl-α-D-ribofuranose with a high concentration of acetic acid yielded 1,2,3-tri-O-acetyl-5-O-benzoyl-3-C-methyl-D-arabinofuranose, which was used for the preparation of 3-C-methyl-α-D-arabinofuranosyl nucleosides. 3'-C-Methylribonucleosides were also synthesized starting from 1,2,3-tri-O-acetyl-5-O-benzoyl-3-C-C-methyl-D-ribofuranose.