کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
1390263 | 1500876 | 2013 | 11 صفحه PDF | دانلود رایگان |
• Multigram syntheses of carbohydrate-based spirooxazolidinones are developed.
• Novel 3-spiropseudonucleosides are characterized by X-ray diffraction analysis.
• User-friendly diacetone-α-d-glucose oxidation is elaborated and validated.
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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Journal: Carbohydrate Research - Volume 375, 28 June 2013, Pages 5–15