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Improved Synthesis of Sulfur-Containing Glycosides by Suppressing Thioacetyl Migration.
Front Chem. 2020; 8:319.FC

Abstract

Complex mixtures were often observed when we attempted to synthesize 4-thio- and 2,4-dithio-glycoside derivatives by double parallel and double serial inversion, thus leading to no or low yields of target products. The reason was later found to be that many unexpected side products were produced when a nucleophile substituted the leaving group on the substrate containing the thioacetate group. We hypothesized that thioacetyl migration is prone to occur due to the labile thioacetate group even under weak basic conditions caused by the nucleophile, leading to this result. Therefore, we managed to inhibit the generation of thiol groups from thioacetate groups by the addition of an appropriate amount of conjugate acid/anhydride, successfully improving the synthesis of 4-thio- and 2,4-dithio-glycoside derivatives. The target products which were previously difficult to synthesize, were herein obtained in relatively high yields. Finally, 4-deoxy- and 2,4-dideoxy-glycoside derivatives were efficiently synthesized through the removal of thioacetate groups under UV light, starting from 4-thio- and 2,4-dithio-glycoside derivatives.

Authors+Show Affiliations

Key Laboratory for Large-Format Battery Materials and System, Ministry of Education, School of Chemistry & Chemical Engineering, Huazhong University of Science and Technology, Wuhan, China.Key Laboratory for Large-Format Battery Materials and System, Ministry of Education, School of Chemistry & Chemical Engineering, Huazhong University of Science and Technology, Wuhan, China.Analysis Center of College of Science & Technology, Hebei Agricultural University, Huanghua, China.Analysis Center of College of Science & Technology, Hebei Agricultural University, Huanghua, China.Key Laboratory for Large-Format Battery Materials and System, Ministry of Education, School of Chemistry & Chemical Engineering, Huazhong University of Science and Technology, Wuhan, China.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

32391332

Citation

Luo, Tao, et al. "Improved Synthesis of Sulfur-Containing Glycosides By Suppressing Thioacetyl Migration." Frontiers in Chemistry, vol. 8, 2020, p. 319.
Luo T, Zhang Y, Xi J, et al. Improved Synthesis of Sulfur-Containing Glycosides by Suppressing Thioacetyl Migration. Front Chem. 2020;8:319.
Luo, T., Zhang, Y., Xi, J., Lu, Y., & Dong, H. (2020). Improved Synthesis of Sulfur-Containing Glycosides by Suppressing Thioacetyl Migration. Frontiers in Chemistry, 8, 319. https://doi.org/10.3389/fchem.2020.00319
Luo T, et al. Improved Synthesis of Sulfur-Containing Glycosides By Suppressing Thioacetyl Migration. Front Chem. 2020;8:319. PubMed PMID: 32391332.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Improved Synthesis of Sulfur-Containing Glycosides by Suppressing Thioacetyl Migration. AU - Luo,Tao, AU - Zhang,Ying, AU - Xi,Jiafeng, AU - Lu,Yuchao, AU - Dong,Hai, Y1 - 2020/04/23/ PY - 2019/12/12/received PY - 2020/03/30/accepted PY - 2020/5/12/entrez PY - 2020/5/12/pubmed PY - 2020/5/12/medline KW - 2,4-dideoxy-glycoside KW - 4-deoxy glycoside KW - acetyl group migration KW - desulfurization KW - sulfur-containing glycoside SP - 319 EP - 319 JF - Frontiers in chemistry JO - Front Chem VL - 8 N2 - Complex mixtures were often observed when we attempted to synthesize 4-thio- and 2,4-dithio-glycoside derivatives by double parallel and double serial inversion, thus leading to no or low yields of target products. The reason was later found to be that many unexpected side products were produced when a nucleophile substituted the leaving group on the substrate containing the thioacetate group. We hypothesized that thioacetyl migration is prone to occur due to the labile thioacetate group even under weak basic conditions caused by the nucleophile, leading to this result. Therefore, we managed to inhibit the generation of thiol groups from thioacetate groups by the addition of an appropriate amount of conjugate acid/anhydride, successfully improving the synthesis of 4-thio- and 2,4-dithio-glycoside derivatives. The target products which were previously difficult to synthesize, were herein obtained in relatively high yields. Finally, 4-deoxy- and 2,4-dideoxy-glycoside derivatives were efficiently synthesized through the removal of thioacetate groups under UV light, starting from 4-thio- and 2,4-dithio-glycoside derivatives. SN - 2296-2646 UR - https://www.unboundmedicine.com/medline/citation/32391332/Improved_Synthesis_of_Sulfur_Containing_Glycosides_by_Suppressing_Thioacetyl_Migration_ L2 - https://doi.org/10.3389/fchem.2020.00319 DB - PRIME DP - Unbound Medicine ER -
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