23393-73-9Relevant articles and documents
Nucleosides 9: Design and synthesis of new 8-nitro and 8-amino xanthine nucleosides of expected biological activity
Mohamed, Mosselhi A. N. M.,Abu-Alola, Laila M. B.,Aljaied, Nada M. G.
, p. 745 - 756 (2017/12/26)
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
Bookser, Brett C.,Raffaele, Nicholas B.
, p. 173 - 179 (2007/10/03)
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.
An efficient method for the synthesis of β-D-ribonucleosides catalyzed by metal iodides
Mukaiyama, Teruaki,Nagai, Masashi,Matsutani, Takafumi,Shimomura, Naoyuki
, p. 17 - 30 (2007/10/03)
Several β-D-ribonucleosides were synthesized in high yields under mild conditions by N-glycosylations of methyl 2,3,5-tri-O-benzoyl-β-D-ribofuranosyl carbonate (1) with trimethylsilylated nucleoside bases in acetonitrile using a catalytic amount of metal iodide such as SnI2, SbI3 or TeI4. A deprotection of N6-benzoyl group of coupling product took place to a considerable extent when N6-benzoyl-N6,N9-bis(trimethylsilyl)adenine was employed as a nucleoside base using SnI2 or SnCI2 as a catalyst while it was minimized when SbI3 or TeI4 was used. Further, the N-glycosylation of 1 with 7-trimethylsilyltheophylline in the presence of a catalytic amount of metal iodide was more effectively achieved in nitrile solvents other than acetonitrile.
Tin(II) Chloride Catalyzed Synthesis of β-D-Ribonucleosides
Mukaiyama, Teruaki,Matsutani, Takafumi,Shimomura, Naoyuki
, p. 2089 - 2092 (2007/10/02)
Several β-D-ribonucleosides are stereoselectively synthesized in high yields from methyl 2,3,5-tri-O-benzoyl-β-D-ribofuranosyl carbonate and trimethylsilylated nucleoside bases such as pertrimethylsilylated uracil and adenine under mild conditions by using a catalytic amount of tin(II) chloride, a weak Lewis acid.
Stereoselective syntheses of β-D-ribonucleosides catalyzed by the combined use of silver salts and diphenyltin sulfide or Lawesson's reagent
Shimomura,Matsutani,Mukaiyama
, p. 3100 - 3106 (2007/10/02)
β-D-Ribonucleosides are stereoselectively synthesized in high yields from methyl 2,3,5-tri-O-benzoyl-β-D-ribofuranosyl carbonate and trimethylsilylated nucleoside bases by the use of [diphenyltin sulfide/silver salt] or [Lawesson's reagent/silver salt] combined catalyst system under mild conditions.
Nucleoside Syntheses, XXII. Nucleoside Synthesis with Trimethylsilyl Triflate and Perchlorate as Catalysts
Vorbrueggen, Helmut,Krolikiewicz, Konrad,Bennua, Baerbel
, p. 1234 - 1255 (2007/10/02)
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.
