Synthesis and structure of 1-deoxy-1-phenyl-β-D-ribofuranose and its incorporation into oligonucleotides

Journal of Organic Chemistry

Volumn 61, Issue 11, 1996, Pages 3909-3911

  Matulic Adamic, Jasenka ^a   Beigelman, Leonid ^a   Portmann, Stefan ^a   Egli, Martin ^a   Usman, Nassim ^a  

^a Sirna Therapeutics Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 DEOXY 1 PHENYL BETA D RIBOFURANOSE; CARBOHYDRATE DERIVATIVE; NUCLEOSIDE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBOHYDRATE SYNTHESIS; DRUG STRUCTURE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; RNA SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0029999204     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960091b     Document Type: Article

References (28)

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16. It should be noted that for hemiacetals 2 the prefix a refers to the position of the glycosidic OH group relative to the configuration at the reference C-atom (C4′ in 2; i.e., the phenyl moiety is in the β-position).
17. 3) resonances for 2′,3′-O-isopropylidene groups of 2: δ 1.68 (s) and 1.40 (s), Δδ = 0.28, α-isomer; 1.38 (s) and 1.25 (s), Δδ = 0.13, β-isomer. For the assignment of the anomeric configuration of nucleosides based on Δδ values, see: Tapiero, C.; Imbach, J.-L. In Nucleic Acid Chemistry, Part 1; Townsend, L. B., Tipson, R. S., Eds.; J. Wiley & Sons, Inc.: New York, 1978; pp 1055-1059. Ohrui, H.; Jones, G. H.; Moffatt, J. G.; Maddox, M. L.; Christensen, A. T.; Byram, S. K. J. Am. Chem. Soc. 1975, 97, 4602-4613.
18. 3) resonances for 2′,3′-O-isopropylidene groups of 2: δ 1.68 (s) and 1.40 (s), Δδ = 0.28, α-isomer; 1.38 (s) and 1.25 (s), Δδ = 0.13, β-isomer. For the assignment of the anomeric configuration of nucleosides based on Δδ values, see: Tapiero, C.; Imbach, J.-L. In Nucleic Acid Chemistry, Part 1; Townsend, L. B., Tipson, R. S., Eds.; J. Wiley & Sons, Inc.: New York, 1978; pp 1055-1059. Ohrui, H.; Jones, G. H.; Moffatt, J. G.; Maddox, M. L.; Christensen, A. T.; Byram, S. K. J. Am. Chem. Soc. 1975, 97, 4602-4613.
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21. 1 and the cell constants were a = 6.736 Å, b = 6.780 Å, c = 11.085 Å, β = 99.64°. Data were collected on an Enraf-Nonius CAD4 diffractometer (Mo Kα) and reduced to 1582 unique reflections (1 ≥ 2σ(1)). The structure was solved with direct methods using the program SHELXS-86 and refined with the program SHELXL-93 (Sheldrick, G. SHELXS-86, Universität Göttingen, Germany, 1986. Sheldrick, G. SHELXL-93, Universität Göttingen, Germany, 1993). The final R-factor was 5.45%.
22. Thibaudeau, C; Plavec, J.; Chattopadhyaya, J. J. Am. Chem. Soc. 1994, 116, 8033-8037 and references cited therein.
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28. The author has deposited atomic coordinates for this structure with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, U.K.