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Synthesis of Core M3 Matriglycan Constituents via an Additive-Controlled 1,2-cis-Xylopyranosylation with O-Xylosyl Imidates as Donors

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2024

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Li, Tianlu
Zhang, Miaomiao
Lv, Panpan
Yang, Yue

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National Natural Science Foundation of China: 92053110
National Natural Science Foundation of China: 22177061
National Natural Science Foundation of China: 21977063

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The Journal of Organic Chemistry. ACS Publications. 2024, 89(1), pp. 804-809. ISSN 0022-3263. eISSN 1520-6904. Available under: doi: 10.1021/acs.joc.3c02339

Zusammenfassung

A highly stereoselective strategy for 1,2-cis-xylopyranoside bond formation was established via a preactivation-based, additive-modulated trichloroacetimidate glycosidation strategy. The current protocol is mild, practical, and successful with various xylopyranosyl donors and glycosyl acceptors, including acceptors that are reported to be less reactive due to steric hindrance. The utility of this method was demonstrated with the facile assembly of matriglycan constituent tetra- and hexasaccharides.

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540 Chemie

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ISO 690LI, Tianlu, Miaomiao ZHANG, Panpan LV, Yue YANG, Richard R. SCHMIDT, Peng PENG, 2024. Synthesis of Core M3 Matriglycan Constituents via an Additive-Controlled 1,2-cis-Xylopyranosylation with O-Xylosyl Imidates as Donors. In: The Journal of Organic Chemistry. ACS Publications. 2024, 89(1), pp. 804-809. ISSN 0022-3263. eISSN 1520-6904. Available under: doi: 10.1021/acs.joc.3c02339
BibTex
@article{Li2024Synth-69177,
  year={2024},
  doi={10.1021/acs.joc.3c02339},
  title={Synthesis of Core M3 Matriglycan Constituents via an Additive-Controlled 1,2-cis-Xylopyranosylation with O-Xylosyl Imidates as Donors},
  number={1},
  volume={89},
  issn={0022-3263},
  journal={The Journal of Organic Chemistry},
  pages={804--809},
  author={Li, Tianlu and Zhang, Miaomiao and Lv, Panpan and Yang, Yue and Schmidt, Richard R. and Peng, Peng}
}
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