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Stereoselective Synthesis of α-3-Deoxy-D-manno-oct-2-ulosonic Acid (α-Kdo) Glycosides Using 5,7-O-Di-tert-butylsilylene-Protected Kdo Ethyl Thioglycoside Donors.
Angew Chem Int Ed Engl. 2015 Sep 07; 54(37):10894-8.AC

Abstract

An efficient methodology for the synthesis of α-Kdo glycosidic bonds has been developed with 5,7-O-di-tert-butylsilylene (DTBS) protected Kdo ethyl thioglycosides as glycosyl donors. The approach permits a wide scope of acceptors to be used, thus affording biologically significant Kdo glycosides in good to excellent chemical yields with complete α-selectivity. The synthetic utility of an orthogonally protected Kdo donor has been demonstrated by concise preparation of two α-Kdo-containing oligosaccharides.

Authors+Show Affiliations

Department of Chemistry of Medicinal Natural Products, Key Laboratory of Drug Targeting and Drug Delivery Systems of the Ministry of Education, West China School of Pharmacy. State Key Laboratory of Biotherapy, West China Hospital, Sichuan University, Chengdu 610041 (China).Department of Chemistry of Medicinal Natural Products, Key Laboratory of Drug Targeting and Drug Delivery Systems of the Ministry of Education, West China School of Pharmacy. State Key Laboratory of Biotherapy, West China Hospital, Sichuan University, Chengdu 610041 (China).Department of Chemistry of Medicinal Natural Products, Key Laboratory of Drug Targeting and Drug Delivery Systems of the Ministry of Education, West China School of Pharmacy. State Key Laboratory of Biotherapy, West China Hospital, Sichuan University, Chengdu 610041 (China).Department of Chemistry of Medicinal Natural Products, Key Laboratory of Drug Targeting and Drug Delivery Systems of the Ministry of Education, West China School of Pharmacy. State Key Laboratory of Biotherapy, West China Hospital, Sichuan University, Chengdu 610041 (China).Department of Chemistry of Medicinal Natural Products, Key Laboratory of Drug Targeting and Drug Delivery Systems of the Ministry of Education, West China School of Pharmacy. State Key Laboratory of Biotherapy, West China Hospital, Sichuan University, Chengdu 610041 (China).Department of Chemistry of Medicinal Natural Products, Key Laboratory of Drug Targeting and Drug Delivery Systems of the Ministry of Education, West China School of Pharmacy. yjs@scu.edu.cn. State Key Laboratory of Biotherapy, West China Hospital, Sichuan University, Chengdu 610041 (China). yjs@scu.edu.cn.

Pub Type(s)

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

Language

eng

PubMed ID

26205626

Citation

Huang, Jia-Sheng, et al. "Stereoselective Synthesis of α-3-Deoxy-D-manno-oct-2-ulosonic Acid (α-Kdo) Glycosides Using 5,7-O-Di-tert-butylsilylene-Protected Kdo Ethyl Thioglycoside Donors." Angewandte Chemie (International Ed. in English), vol. 54, no. 37, 2015, pp. 10894-8.
Huang JS, Huang W, Meng X, et al. Stereoselective Synthesis of α-3-Deoxy-D-manno-oct-2-ulosonic Acid (α-Kdo) Glycosides Using 5,7-O-Di-tert-butylsilylene-Protected Kdo Ethyl Thioglycoside Donors. Angew Chem Int Ed Engl. 2015;54(37):10894-8.
Huang, J. S., Huang, W., Meng, X., Wang, X., Gao, P. C., & Yang, J. S. (2015). Stereoselective Synthesis of α-3-Deoxy-D-manno-oct-2-ulosonic Acid (α-Kdo) Glycosides Using 5,7-O-Di-tert-butylsilylene-Protected Kdo Ethyl Thioglycoside Donors. Angewandte Chemie (International Ed. in English), 54(37), 10894-8. https://doi.org/10.1002/anie.201505176
Huang JS, et al. Stereoselective Synthesis of α-3-Deoxy-D-manno-oct-2-ulosonic Acid (α-Kdo) Glycosides Using 5,7-O-Di-tert-butylsilylene-Protected Kdo Ethyl Thioglycoside Donors. Angew Chem Int Ed Engl. 2015 Sep 7;54(37):10894-8. PubMed PMID: 26205626.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Stereoselective Synthesis of α-3-Deoxy-D-manno-oct-2-ulosonic Acid (α-Kdo) Glycosides Using 5,7-O-Di-tert-butylsilylene-Protected Kdo Ethyl Thioglycoside Donors. AU - Huang,Jia-Sheng, AU - Huang,Wei, AU - Meng,Xue, AU - Wang,Xin, AU - Gao,Peng-Cheng, AU - Yang,Jin-Song, Y1 - 2015/07/23/ PY - 2015/06/06/received PY - 2015/7/25/entrez PY - 2015/7/25/pubmed PY - 2016/5/21/medline KW - acetals KW - carbohydrates KW - glycosylation KW - silanes KW - synthesis design SP - 10894 EP - 8 JF - Angewandte Chemie (International ed. in English) JO - Angew. Chem. Int. Ed. Engl. VL - 54 IS - 37 N2 - An efficient methodology for the synthesis of α-Kdo glycosidic bonds has been developed with 5,7-O-di-tert-butylsilylene (DTBS) protected Kdo ethyl thioglycosides as glycosyl donors. The approach permits a wide scope of acceptors to be used, thus affording biologically significant Kdo glycosides in good to excellent chemical yields with complete α-selectivity. The synthetic utility of an orthogonally protected Kdo donor has been demonstrated by concise preparation of two α-Kdo-containing oligosaccharides. SN - 1521-3773 UR - https://www.unboundmedicine.com/medline/citation/26205626/Stereoselective_Synthesis_of_α_3_Deoxy_D_manno_oct_2_ulosonic_Acid__α_Kdo__Glycosides_Using_57_O_Di_tert_butylsilylene_Protected_Kdo_Ethyl_Thioglycoside_Donors_ L2 - https://doi.org/10.1002/anie.201505176 DB - PRIME DP - Unbound Medicine ER -