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Open AccessArticle

Total Synthesis of Natural Disaccharide Sambubiose

Department of Biomolecular Sciences, University of Urbino Carlo Bo Piazza del Rinascimento, 6, 61029 Urbino, Italy
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Authors to whom correspondence should be addressed.
These authors contributed equally to this work.
Pharmaceuticals 2020, 13(8), 198; https://doi.org/10.3390/ph13080198
Received: 23 June 2020 / Revised: 12 August 2020 / Accepted: 13 August 2020 / Published: 17 August 2020
(This article belongs to the Section Natural Products)
A practical and robust synthetic method to obtain the natural disaccharide sambubiose (2-O-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-D-xylopiranosyl-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. View Full-Text
Keywords: chemopreventive phytochemicals; flavonoids; 2-O-xylosylvitexin; antiproliferative activity; carbohydrates; glycosylation; sambubiose; total synthesis chemopreventive phytochemicals; flavonoids; 2-O-xylosylvitexin; antiproliferative activity; carbohydrates; glycosylation; sambubiose; total synthesis
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MDPI and ACS Style

Lucarini, S.; Ciulla, M.G.; Mestichelli, P.; Duranti, A. Total Synthesis of Natural Disaccharide Sambubiose. Pharmaceuticals 2020, 13, 198.

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