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

✍ Scribed by Kenichi Takeo; Yasushi Ohguchi; Rumi Hasegawa; Shinichi Kitamura

Publisher: Elsevier Science
Year: 1995
Tongue: English
Weight: 835 KB
Volume: 277
Category: Article
ISSN: 0008-6215
DOI: 10.1016/0008-6215(95)00214-e

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✦ Synopsis

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.

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