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Stereoselective synthesis of α-linked 2-deoxy glycosides enabled by visible-light-mediated reductive deiodination.
Chemistry. 2014 Dec 22; 20(52):17319-23.C

Abstract

2-Deoxy sugars and their derivatives occur abundantly in many pharmaceutically important natural products. However, the construction of specific 2-deoxy-glycosidic bonds remains as a challenge. Herein, we report an efficient way to prepare 2-deoxy-α-glycosides by glycosylation of 2-iodo-glycosyl acetate and subsequent visible-light-mediated tin-free reductive deiodination. We have successfully applied the postglycosylational-deiodination strategy in the synthesis of more than 30 mono-, di-, tri-, tetra- and pentadeoxysaccharides with excellent stereoselectivity and efficiency. This method has also been applied to the synthesis of a 2-deoxy-tetrasaccharide containing four α-linkages.

Authors+Show Affiliations

Tongji School of Pharmacy, Huazhong University of Science and Technology, 13 Hangkong Road, Wuhan, Hubei, 430030 (P. R. China).No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

25377922

Citation

Wang, Hao, et al. "Stereoselective Synthesis of Α-linked 2-deoxy Glycosides Enabled By Visible-light-mediated Reductive Deiodination." Chemistry (Weinheim an Der Bergstrasse, Germany), vol. 20, no. 52, 2014, pp. 17319-23.
Wang H, Tao J, Cai X, et al. Stereoselective synthesis of α-linked 2-deoxy glycosides enabled by visible-light-mediated reductive deiodination. Chemistry. 2014;20(52):17319-23.
Wang, H., Tao, J., Cai, X., Chen, W., Zhao, Y., Xu, Y., Yao, W., Zeng, J., & Wan, Q. (2014). Stereoselective synthesis of α-linked 2-deoxy glycosides enabled by visible-light-mediated reductive deiodination. Chemistry (Weinheim an Der Bergstrasse, Germany), 20(52), 17319-23. https://doi.org/10.1002/chem.201405516
Wang H, et al. Stereoselective Synthesis of Α-linked 2-deoxy Glycosides Enabled By Visible-light-mediated Reductive Deiodination. Chemistry. 2014 Dec 22;20(52):17319-23. PubMed PMID: 25377922.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Stereoselective synthesis of α-linked 2-deoxy glycosides enabled by visible-light-mediated reductive deiodination. AU - Wang,Hao, AU - Tao,Jinyi, AU - Cai,Xinpei, AU - Chen,Wei, AU - Zhao,Yueqi, AU - Xu,Yang, AU - Yao,Wang, AU - Zeng,Jing, AU - Wan,Qian, Y1 - 2014/11/05/ PY - 2014/10/03/received PY - 2014/11/8/entrez PY - 2014/11/8/pubmed PY - 2015/8/15/medline KW - deiodination KW - glycosides KW - glycosylation KW - photocatalysis KW - radical reaction SP - 17319 EP - 23 JF - Chemistry (Weinheim an der Bergstrasse, Germany) JO - Chemistry VL - 20 IS - 52 N2 - 2-Deoxy sugars and their derivatives occur abundantly in many pharmaceutically important natural products. However, the construction of specific 2-deoxy-glycosidic bonds remains as a challenge. Herein, we report an efficient way to prepare 2-deoxy-α-glycosides by glycosylation of 2-iodo-glycosyl acetate and subsequent visible-light-mediated tin-free reductive deiodination. We have successfully applied the postglycosylational-deiodination strategy in the synthesis of more than 30 mono-, di-, tri-, tetra- and pentadeoxysaccharides with excellent stereoselectivity and efficiency. This method has also been applied to the synthesis of a 2-deoxy-tetrasaccharide containing four α-linkages. SN - 1521-3765 UR - https://www.unboundmedicine.com/medline/citation/25377922/Stereoselective_synthesis_of_α_linked_2_deoxy_glycosides_enabled_by_visible_light_mediated_reductive_deiodination_ L2 - https://doi.org/10.1002/chem.201405516 DB - PRIME DP - Unbound Medicine ER -