Vitamin B12-catalyzed synthesis of some peracetylated alkyl β-D-xylopyranosides

• Main Authors: Petrović Zorica D., Anđelković Dejan, Stevanović Ljiljana
• Format: Article
• Language: English
• Published: Serbian Chemical Society 2003-01-01
• Series: Journal of the Serbian Chemical Society
• Subjects: alkyl β-d-xylopyranosides; brominated β-d-xylose peracetate; glycosylaton; vitamin b12
• Online Access: http://www.doiserbia.nb.rs/img/doi/0352-5139/2003/0352-51390310719P.pdf

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 %).