3001-44-3

Usage

InChI:InChI=1/C12H16N4O6/c1-15-10-5(11(20)16(2)12(15)21)13-9(14-10)8-7(19)6(18)4(3-17)22-8/h4,6-8,17-19H,3H2,1-2H3,(H,13,14)/t4-,6-,7-,8?/m1/s1

Upstream product

• 6974-32-9 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose 
• 13035-61-5 1,2,3,5-tetraacetylribose 
• 88154-61-4 6-Amino-1,3-dimethyl-5-[(2S,3S,4R)-2,3,4,5-tetrahydroxy-pent-(Z)-ylideneamino]-1H-pyrimidine-2,4-dione 
• 62374-32-7 1,3-dimethyl-7-(trimethylsilyl)xanthine 
• 50-69-1 D-ribose 
• 5440-00-6 4,5-Diamino-1,3-dimethyluracil 
• 58-55-9 theophylline 
• 58-55-9 Theophylline 
• 636603-96-8 7-[5'-acetyl-2',3'-O-(ethoxymethylidene)-β-D-ribofuranosyl]theophylline 
• 14036-06-7 diethoxymethyl acetate 
• 23393-73-9 N²-acetyl-2',3',5'-tri-O-benzoyl-β-D-guanosine 
• 30725-02-1 7-(2',3',4'-tri-O-acetyl-β-D-ribofuranosyl)theophylline 

Downstream Products

• 122147-11-9 7-[O²,O³-isopropylidene-O⁵-(toluene-4-sulfonyl)-β-D-ribofuranosyl]-1,3-dimethyl-3,7-dihydro-purine-2,6-dione 

Relevant academic research and scientific papers

Nucleosides 9: Design and synthesis of new 8-nitro and 8-amino xanthine nucleosides of expected biological activity

The coupling reaction of 1,3-dimethylxanthine (theophylline), 3-benzylxanthine and 3-benzyl-1-methylxanthine with 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose afforded the corresponding protected nucleosides, respectively. Nitration of each of the theo

High-throughput five minute microwave accelerated glycosylation approach to the synthesis of nucleoside libraries

The Vorbrueggen glycosylation reaction was adapted into a one-step 5 min/130 °C microwave assisted reaction. Triethanolamine in acetontrile containing 2% water was determined to be optimal for the neutralization of trimethylsilyl inflate allowing for direct MPLC purification of the reaction mixture. When coupled with a NH3/methanol deprotection reaction, a high-throughput method of nucleoside library synthesis was enabled. The method was demonstrated by examining the ribosylation of 48 nitrogen containing heteroaromatic bases that included 25 purines, four pyrazolopyrimidines, two 8-azapurines, one 2-azapurine, two imidazopyridines, two benzimidazoles, three imidazoles, three 1,2,4-triazoles, two pyrimidines, two 3-deazapyrimidines, one quinazolinedione, and one alloxazine. Of these, 32 yielded single regioisomer products, and six resulted in separable mixtures. Seven examples provided inseparable regioisomer mixtures of -two to three compounds (16 nucleosides), and three examples failed to yield isolable products. For the 45 single isomers isolated, the average two-step overall yield ± SD was 26 ± 16%, and the average purity ± SD was 95 ± 6%. A total of 58 different nucleosides were prepared of which 15 had not previously been accessed directly from glycosylation/deprotection of a readily available base.

Synthesis of Theophylline and 6-Thiotheophylline 7-Ribosyl Nucleosides

The syntheses of theophylline and thiotheophylline 7-ribopyranose and 7-ribofuranose nucleosides, both by direct coupling of the base and the sugar and by construction of the imidazole ring, are reported. The conformational syn/anti equilibrium of the peracetyl derivatives was studied by molecular mechanics and by the low-temperature line-shape/1H NMR method. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.

Nucleoside Syntheses, XXII. Nucleoside Synthesis with Trimethylsilyl Triflate and Perchlorate as Catalysts

The novel Lewis acids (CH3)3SiOSO2CF3 (5), (CH3)3SiOSO2C4F9 (6), and (CH3)3SiClO4 (4) are highly selective and efficient Friedel-Crafts catalysts for nucleoside formation from silylated heterocycles and peracylated sugars as well as for rearrangements of persilylated protected nucleosides.With basic silylated heterocycles these new catalysts give much higher yields of the natural N-1-nucleosides than with SnCl4.