Takeo K, Ohguchi Y, Hasegawa R, Kitamura S
Department of Agricultural Chemistry, Kyoto Prefectural University, Japan.
Carbohydr Res. 1995 Nov 22;277(2):231-44. doi: 10.1016/0008-6215(95)00214-e.
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.
2-和4-硝基苯基β-D-吡喃木糖苷（4和5）通过二丁基氧化锡介导的酰化反应转化为相应的2,3-二-O-苯甲酰基衍生物11和15。木二糖和木三糖通过木炭柱色谱法从市售原料中轻松分离出来，并转化为二糖和三糖甲基1-硫代-β-糖苷36和37。以11和15为糖基受体，1-硫代-β-D-吡喃木糖苷三乙酸酯16、36和37为糖基供体，通过N-碘代琥珀酰亚胺-三氟甲磺酸银促进的缩合反应合成了聚合度为2-4的β-(1→4)-D-木糖寡糖的2-和4-硝基苯基β-糖苷。还描述了4和5的改进制备方法、1-萘基β-D-吡喃木糖苷的合成，以及2-和4-硝基苯基β-木二糖苷的另一种合成方法。
