Vitamin B12-catalyzed synthesis of some peracetylated alkyl β-D-xylopyranosides
| Autor: | Petrović Zorica D., Anđelković Dejan, Stevanović Ljiljana |
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| Jazyk: | angličtina |
| Rok vydání: | 2003 |
| Předmět: | |
| Zdroj: | Journal of the Serbian Chemical Society, Vol 68, Iss 10, Pp 719-722 (2003) |
| Druh dokumentu: | article |
| ISSN: | 0352-5139 1820-7421 |
| DOI: | 10.2298/JSC0310719P |
| Popis: | The vitamin B12-catalyzed glycosylation reaction of brominated β-D-xylose peracetate with alkanols ROH (C1-C8) has been studied. The catalytically active species in this reaction was cob(I)alamin, obtained by chemical reduction of Vitamin B12 with NaBH4 (Co(III) to Co(I)). The reaction was carried out with 2 mol% of vitamin B12, with respect to xylosyl bromide 1 under argon at room temperature. Under these conditions, peracetylated C1-C8-alkyl β-D-xylopyranosides (3a–3f) were obtained in moderate yield (55–70 %). In all cases 3,4-di-O-acetyl-D-xylal (4) was obtained, as the product of reductive elimination of peracetylated xylosyl bromide (15–25 %). |
| Databáze: | Directory of Open Access Journals |
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