Synthesis of 2- and 4-nitrophenyl β-glycosides of β-(1 → 4)-D-xylo-oligosaccharides of dp 2-4

Article abstract of DOI:10.1016/0008-6215(95)00214-E

2- and 4-Nitrophenyl β-D-xylopyranosides (4 and 5) were transformed, via dibutyltin oxide-mediated acylation, into the corresponding 2,3-di-O-benzoyl derivatives 11 and 15. Xylobiose and xylotriose were easily isolated by charcoal column chromatography from a commercially available material and converted into the di- and trisaccharide methyl 1-thio-β-glycosides 36 and 37. The 2- and 4-nitrophenyl β-glycosides of the β-(1 → 4)-D-xylo-oligosaccharides of dp 2-4 were synthesized by N-iodosuccinimide-silver triflate-promoted condensation using 11 and 15 as the glycosyl acceptors and ethyl 1-thio-β-D-xylopyranoside triacetate 16, 36, and 37 as the glycosyl donors. Also described are an improved preparation of 4 and 5, and the synthesis of 1-naphthyl β-D-xylopyranoside, as well as an alternative approach to the 2- and 4-nitrophenyl β-xylobiosides.