Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 18, Issue 1, Pages 108-126Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c9ob02422k
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Funding
- National Natural Science Foundation of China [21762024, 21572081, 21877055]
- Natural Science Foundation of Jiangxi Province [20161ACB20005, 20171BCB23036, 20171BAB203008, 20181BCB24004]
- Innovative Fund of Jiangxi Province [YC2018-S181]
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With easily available monosaccharides and steviol as starting materials, the first total synthesis of rebaudioside R with a xylosyl core in the C13-OH linked sugar chain was accomplished via two distinct approaches. The first approach features the stepwise installation of branch-sugar residues via an order of C2-OH first and then C3-OH of the xylosyl core, laying a firm foundation for the synthesis of analogues with different branch sugars, while the second route features the introduction of the C13 trisaccharide sugar chain via a convergent strategy, securing the overall synthetic efficiency. Through the synthetic study, the effect of protecting groups (PGs) at the vicinal hydroxy group on the reactivity of OH acceptors was illustrated.
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