Synthesis of 2- and 4-nitrophenyl beta-glycosides of beta-(1-->4)- D-xylo-oligosaccharides of dp 2-4.
2- and 4-Nitrophenyl beta-D-xylopyranosides (4 and 5) were transformed, via dibutyltin oxidemediated 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-beta-glycosides 36 and 37. The 2-and 4-nitrophenyl beta-glycosides of the beta-(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-beta-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 beta-D-xylopyranoside, as well as an alternative approach to the 2- and 4-nitrophenyl beta-xylobiosides.
Takeo
K
K
Department of Agricultural Chemistry, Kyoto Prefectural University, Japan.
Ohguchi
Y
Y
Hasegawa
R
R
Kitamura
S
S
D002240:Carbohydrate Sequence; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D009284:Naphthols / Q000138:chemical synthesis; D009596:Nitrophenols / Q000138:chemical synthesis; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D009947:Organotin Compounds / Q000737:chemistry
D006027:Glycosides; D009284:Naphthols; D009596:Nitrophenols; D009844:Oligosaccharides; D009947:Organotin Compounds; C010807:xylosides; C031078:dibutyltin oxide