Biopolym. Cell. 1996; 12(1):86-88.
Directed synthesis of 1 -O-acetyl-2, 3,5-tri-O-benzoyl-β-L-ribofuranose
- Institute of Molecular Biology and Genetics, NAS of Ukraine
150, Akademika Zabolotnoho Str., Kyiv, Ukraine, 03680
Abstract
A new method for the synthesis of 1-O-acetyl-2, 3, 5-tri-O-benzoyl-β-L-ribofwanose has been proposed. Trlfluoromethanesulfonic group was used to invers configuration at C2 of methyl 3, 5-O-(tetraisopropyl-disilox-1, 3-diyl)-L-arabino-furanoside.
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References
[1]
Ashley GW. Modeling, synthesis, and hybridization properties of (L)-ribonucleic acid. J Am Chem Soc. 1992;114(25):9731–6.
[2]
Urata H, Ogura E, Shinohara K, Ueda Y, Akagi M. Synthesis and properties of mirror-image DNA. Nucleic Acids Res. 1992;20(13):3325-32.
[3]
Garbesi A, Capobianco ML, Colonna FP, Tondelli L, Arcamone F, Manzini G, Hilbers CW, Aelen JM, Blommers MJ. L-DNAs as potential antimessenger oligonucleotides: a reassessment. Nucleic Acids Res. 1993;21(18):4159-65.
[4]
Markiewicz WT, Wiewiorowski M. A new type of silyl protecting groups in nucleoside chemistry. Nucleic Acids Res. 1978;1(suppl):s185–s190.
[5]
Hough L. and Richardson A.C Comprehensive Organic Chemistry. Barton D. and Ollis W.D. Khimiya. 1986. 11: 140-7.
[6]
AS. 152J739 USSR. Methyl 5-0-benzyl-2-0-benzoyl-3-fluoro-3-A and dsaoksi BD- ribofuranoside as intermediates in the synthesis of biological assets of 3-fluoro-3-deoxyribonucleosides. NU Pupeyko, TI Prikota, TT Sivets et al. B. 11. 1989. N 30: 42.
[7]
Herdewijn P, Van Aerschot A. Some examples of the use of trifluoromethane sulfonic anhydride in nucleic acid chemistry. Nucleosides, Nucleotides & Nucleic Acids. 1989;8(5):933–7.
[8]
Ryan KJ, Action EM. Syntetic procedure in nucleic acid Chemistry. Eds W. W. Zorbach, R. S. Tipson. New York; London: John Wiley and Sons, 1968. Vol. 1: 163-7.
[9]
Recondo EF, Rinderknecht H. Eine neue, einfache Synthese des. 1-O-Acetyl-2,3,5-Tri-O-benzoyl-?-D-Ribofuranosides. Helv Chim Acta. 1959;42(4):1171–3.
