Carbohydrate Research p. 5 - 15 (2013)
Update date:2022-09-26
Topics:
Turks, Maris
Rodins, Vitalijs
Rolava, Evija
Ostrovskis, Pavels
Belyakov, Sergey
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.
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Doi:10.1016/S0957-4166(00)80442-5
(1990)Doi:10.1016/S0957-4166(00)82381-2
(1990)Doi:10.1002/chem.200800918
(2008)Doi:10.1021/ol2020187
(2011)Doi:10.1002/ejoc.200901372
(2010)Doi:10.1016/j.tetlet.2010.03.030
(2010)