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Publikācija: A Practical Access to Glucose- and Allose-Based (5+5) 3-Spiropseudonucleosides from a Common Intermediate

Publication Type Scientific article indexed in SCOPUS or WOS database
Funding for basic activity Unknown
Defending: ,
Publication language English (en)
Title in original language A Practical Access to Glucose- and Allose-Based (5+5) 3-Spiropseudonucleosides from a Common Intermediate
Field of research 1. Natural sciences
Sub-field of research 1.4 Chemical sciences
Authors Māris Turks
Vitalijs Rodins
Evija Rolava
Pāvels Ostrovskis
Sergejs Beļakovs
Keywords spiropseudonucleosides, spirooxazolidinones, oxidation of diacetone-α-D-glucose, Henry reaction, carbamates, N-acyl-oxazolidinones
Abstract A practical access to glucose-based and allose-based spirooxazolidinones is reported. The synthetic sequence consisting of TEMPO-catalyzed oxidation of 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose, Henry reaction and reduction provides amino alcohol with allo-configuration on a multigram scale. Alternatively, water elimination from Henry products followed by a rehydration gives an access to diastereomerically pure glucose-based nitro alcohol which upon reduction provides complementary amino alcohol with gluco-configuration. The latter amino alcohols are transformed into spirooxazolidinones (3-spiropseudonucleosides) via their N-Cbz or N-phenylcarbamate derivatives. The title compounds easily undergo N-derivatization and give highly crystalline materials. Two of the newly obtained (5+5) 3-spiropseudonucleosides are characterized by X-ray crystallography.
DOI: 10.1016/j.carres.2013.04.008
Hyperlink: http://www.sciencedirect.com/science/article/pii/S0008621513001365 
Reference Turks, M., Rodins, V., Rolava, E., Ostrovskis, P., Beļakovs, S. A Practical Access to Glucose- and Allose-Based (5+5) 3-Spiropseudonucleosides from a Common Intermediate. Carbohydrate Research, 2013, Vol.375, pp.5-15. ISSN 0008-6215. Available from: doi:10.1016/j.carres.2013.04.008
Additional information Citation count:
ID 15850