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Regioselective benzoylation of unprotected β-glycopyranosides with benzoyl cyanide and an amine catalyst : application to saponin synthesis

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Regioselective benzoylation of unprotected β-glycopyranosides with benzoyl cyanide and an amine catalyst : application to saponin synthesis

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LI, Tianlu, Tong LI, Yajing SUN, Yue YANG, Panpan LV, Fengshan WANG, Hongxiang LOU, Richard R. SCHMIDT, Peng PENG, 2021. Regioselective benzoylation of unprotected β-glycopyranosides with benzoyl cyanide and an amine catalyst : application to saponin synthesis. In: Organic Chemistry Frontiers. Royal Society of Chemistry (RSC). 8(2), pp. 260-265. ISSN 2052-4110. eISSN 2052-4129. Available under: doi: 10.1039/D0QO01243B

@article{Li2021Regio-52860, title={Regioselective benzoylation of unprotected β-glycopyranosides with benzoyl cyanide and an amine catalyst : application to saponin synthesis}, year={2021}, doi={10.1039/D0QO01243B}, number={2}, volume={8}, issn={2052-4110}, journal={Organic Chemistry Frontiers}, pages={260--265}, author={Li, Tianlu and Li, Tong and Sun, Yajing and Yang, Yue and Lv, Panpan and Wang, Fengshan and Lou, Hongxiang and Schmidt, Richard R. and Peng, Peng} }

Wang, Fengshan Peng, Peng Lv, Panpan Schmidt, Richard R. 2021-02-17T08:08:45Z Regioselective benzoylation of unprotected β-glycopyranosides with benzoyl cyanide and an amine catalyst : application to saponin synthesis Sun, Yajing Lou, Hongxiang Schmidt, Richard R. Peng, Peng 2021-02-17T08:08:45Z Li, Tong Lv, Panpan Yang, Yue Wang, Fengshan eng Lou, Hongxiang Sun, Yajing Li, Tianlu Li, Tong Li, Tianlu Yang, Yue Protection of totally unprotected β-D-gluco-, β-D-quinovo- and β-D-xylopyranosides with BzCN and Et<sub>3</sub>N as the catalyst afforded directly and regioselectively 3,6-di-O-benzoylated β-D-glucopyranosides or 3-O-benzoylated β-D-quinovo- and β-D-xylopyranosides, respectively. Furthermore, these trans–trans triol and tetrol systems could be regioselectively transformed into their corresponding 2-O-unprotected derivatives in the presence of BzCN as the benzoylating agent and a catalytic amount of 4-pyrrolidinopyridine as a base in one-pot reactions. Hence, BzCN in the presence of a catalytic amount of an amine base exhibits unique properties as an acylating agent, permitting the regioselective protection of all diol, triol and tetrol stereostructures occurring in the commonly found glycopyranosides. The convenient access and great value of some of the derived building blocks are shown through the concise synthesis of natural and unnatural saponins. 2021

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