A short synthesis of protected 3-deoxy-d-arabino-2-heptulosonates (DAH) from shikimic acid based on silyl group migration |
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| Authors: | Jozef Gonda Miroslav Psotka Miroslava Martinková Simona Fazekašová Tatiana Mitríková Mária Vilková |
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| Affiliation: | 1. Department of Organic Chemistry, P. J. ?afárik University, Moyzesova 11, 040 01 Ko?ice, Slovak Republic;2. Biomedical Research Centre, University Hospital Hradec Kralove, Sokolska 581, 50 005 Hradec Králove, Czech Republic |
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| Abstract: | The reaction of (2S,3S,4R)-2,3,4,7-tetrahydroxy-6-oxoheptanals with lower alcohols produced protected 3-deoxy-d-arabino-2-heptulosonates. The key transformation is based on an 1,4-O–O silyl group migration, followed by 6-exo-trig cyclisation to give the final pyranose. |
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| Keywords: | Oxoheptanals Heptulosonates Silyl group migration Corresponding author. |
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