Synthesis of anhydro psicofuranosyl nucleosides

Tetrahedron Letters

Volumn 43, Issue 37, 2002, Pages 6553-6555

  Roivainen, Jarkko ^a   Vepsäläinen, Jouko ^a   Azhayev, Alex ^a   Mikhailopulo, Igor A ^b  

^a UNIVERSITY OF EASTERN FINLAND   (Finland)

^b INSTITUTE OF BIOORGANIC CHEMISTRY   (Belarus)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; ADENINE DERIVATIVE; BROMINE DERIVATIVE; CARBOHYDRATE DERIVATIVE; METHYL 1 O MESYL 5 O TOLUOYL BETA DEXTRO PSICOFURANOSIDE; NUCLEOSIDE DERIVATIVE; THYMINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DEPROTECTION REACTION; DRUG SYNTHESIS; PRECURSOR; SILYLATION;

EID: 0037048511     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)01472-7     Document Type: Article

References (10)

1. Leumann C.J. Bioorg. Med. Chem. 10:2002;841-854.
2. Orum H., Wengel J. Curr. Opin. Mol. Ther. 3:2001;239-243.
3. Rajwanshi V.K., Hakansson A.E., Sorensen M.D., Pitsch S., Singh S.K., Kumar R., Nielsen P., Wengel J. Angew. Chem., Int. Ed. Engl. 39:2000;1656-1659.
4. Prisbe E.J., Smejkal J., Verheyden J.P.H., Moffatt J.G. J. Org. Chem. 41:1976;1836-1846.
5. Azhayev A., Guzaev A., Hovinen J., Mattinen J., Sillanpää R., Lönnberg H. Synthesis. 1994;396-400′
6. TMS, ppm: 158.64 (C-6), 156.02 (C-2), 151.56 (C-4), 142.48 (C-8), 121.57 (C-5), 91.40 (C-3′), 85.84 (C-5′), 82.37 (C-1′), 73.18 (C-4′), 63.13 (C-6′), the low intensity resonance of C-2′ is either overlapped by the resonances of the other pentofuranose carbons, or is absent due to the long relaxation time.
7. 3).
8. 3).
9. . A similar cyclisation was recently observed in the case of a related 3′-deoxynucleoside: Kvaerno L., Wightman R.H., Wengel J. J. Org. Chem. 66:2001;5106-5112.
10. 3).