A practical and robust synthetic method to obtain the natural disaccharide sambubiose (2O-β-D-xylopyranosyl-D-glucopyranose) is reported, exploring the key step in the synthesis, i.e., stereoselective O-glycosylation. Specifically, the best combinations of glycoside donors and acceptors were identified, stereospecific control of the reaction was achieved by screening several catalysts and protection/deprotection steps were evaluated and improved. The best result was obtained by coupling allyl 3,5,6-tri-O-benzyl-β-D-glucofuranoside with 2,3,4-tri-O-acetyl-Dxylopiranosyl-α-trichloro acetimidate in the presence of trimethylsilyl triflate as a catalyst giving the corresponding protected target compound as a correct single isomer. The latter was transformed accordingly into the desired final product by deprotection steps (deallylation, deacetylation, and debenzylation). Sambubiose was synthesized into a satisfactory and higher overall yield than previously reported and was also characterized.

Total synthesis of natural disaccharide sambubiose / S. Lucarini, M.G. Ciulla, P. Mestichelli, A. Duranti. - In: PHARMACEUTICALS. - ISSN 1424-8247. - 13:8(2020 Aug 17), pp. 198.1-198.13. [10.3390/ph13080198]

Total synthesis of natural disaccharide sambubiose

M.G. Ciulla
Co-primo
;
2020

Abstract

A practical and robust synthetic method to obtain the natural disaccharide sambubiose (2O-β-D-xylopyranosyl-D-glucopyranose) is reported, exploring the key step in the synthesis, i.e., stereoselective O-glycosylation. Specifically, the best combinations of glycoside donors and acceptors were identified, stereospecific control of the reaction was achieved by screening several catalysts and protection/deprotection steps were evaluated and improved. The best result was obtained by coupling allyl 3,5,6-tri-O-benzyl-β-D-glucofuranoside with 2,3,4-tri-O-acetyl-Dxylopiranosyl-α-trichloro acetimidate in the presence of trimethylsilyl triflate as a catalyst giving the corresponding protected target compound as a correct single isomer. The latter was transformed accordingly into the desired final product by deprotection steps (deallylation, deacetylation, and debenzylation). Sambubiose was synthesized into a satisfactory and higher overall yield than previously reported and was also characterized.
2-O-xylosylvitexin; antiproliferative activity; carbohydrates; chemopreventive phytochemicals; flavonoids; glycosylation; sambubiose; total synthesis
Settore CHIM/06 - Chimica Organica
17-ago-2020
Article (author)
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/952974
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