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A One-Pot Method for Removal of Thioacetyl Group via Desulfurization under Ultraviolet Light To Synthesize Deoxyglycosides.
Org Lett 2019; 21(15):5903-5906OL

Abstract

We herein developed an efficient method for removing thioacetyl to synthesize acylated deoxy glycosides in a one-pot reaction, where the thioacetyl was selectively deacetylated by hydrazine hydrate in DMF within 2-5 min at room temperature, followed by desulfurization under UV light for 1-2 h in the presence of TCEP·HCl. The method was then used to synthesize 2-deoxy glycosides with absolute α/β-configuration via stereoselective control of C-2 thioacetate in glycosylation.

Authors+Show Affiliations

Key laboratory of Material Chemistry for Energy Conversion and Storage, Ministry of Education, Hubei Key Laboratory of Bioinorganic Chemistry & Materia Medica, School of Chemistry & Chemical Engineering , Huazhong University of Science & Technology , Luoyu Road 1037 , Wuhan , 430074 , P. R. China. School of Chemistry and Chemical Engineering , Hubei Polytechnic University , Guilinbei Road 16 , Huangshi , 435003 , P. R. China.Key laboratory of Material Chemistry for Energy Conversion and Storage, Ministry of Education, Hubei Key Laboratory of Bioinorganic Chemistry & Materia Medica, School of Chemistry & Chemical Engineering , Huazhong University of Science & Technology , Luoyu Road 1037 , Wuhan , 430074 , P. R. China.Key laboratory of Material Chemistry for Energy Conversion and Storage, Ministry of Education, Hubei Key Laboratory of Bioinorganic Chemistry & Materia Medica, School of Chemistry & Chemical Engineering , Huazhong University of Science & Technology , Luoyu Road 1037 , Wuhan , 430074 , P. R. China.Key laboratory of Material Chemistry for Energy Conversion and Storage, Ministry of Education, Hubei Key Laboratory of Bioinorganic Chemistry & Materia Medica, School of Chemistry & Chemical Engineering , Huazhong University of Science & Technology , Luoyu Road 1037 , Wuhan , 430074 , P. R. China.Key laboratory of Material Chemistry for Energy Conversion and Storage, Ministry of Education, Hubei Key Laboratory of Bioinorganic Chemistry & Materia Medica, School of Chemistry & Chemical Engineering , Huazhong University of Science & Technology , Luoyu Road 1037 , Wuhan , 430074 , P. R. China.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

31310551

Citation

Ge, Jian-Tao, et al. "A One-Pot Method for Removal of Thioacetyl Group Via Desulfurization Under Ultraviolet Light to Synthesize Deoxyglycosides." Organic Letters, vol. 21, no. 15, 2019, pp. 5903-5906.
Ge JT, Zhou L, Luo T, et al. A One-Pot Method for Removal of Thioacetyl Group via Desulfurization under Ultraviolet Light To Synthesize Deoxyglycosides. Org Lett. 2019;21(15):5903-5906.
Ge, J. T., Zhou, L., Luo, T., Lv, J., & Dong, H. (2019). A One-Pot Method for Removal of Thioacetyl Group via Desulfurization under Ultraviolet Light To Synthesize Deoxyglycosides. Organic Letters, 21(15), pp. 5903-5906. doi:10.1021/acs.orglett.9b02033.
Ge JT, et al. A One-Pot Method for Removal of Thioacetyl Group Via Desulfurization Under Ultraviolet Light to Synthesize Deoxyglycosides. Org Lett. 2019 Aug 2;21(15):5903-5906. PubMed PMID: 31310551.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - A One-Pot Method for Removal of Thioacetyl Group via Desulfurization under Ultraviolet Light To Synthesize Deoxyglycosides. AU - Ge,Jian-Tao, AU - Zhou,Lang, AU - Luo,Tao, AU - Lv,Jian, AU - Dong,Hai, Y1 - 2019/07/16/ PY - 2019/7/17/pubmed PY - 2019/7/17/medline PY - 2019/7/17/entrez SP - 5903 EP - 5906 JF - Organic letters JO - Org. Lett. VL - 21 IS - 15 N2 - We herein developed an efficient method for removing thioacetyl to synthesize acylated deoxy glycosides in a one-pot reaction, where the thioacetyl was selectively deacetylated by hydrazine hydrate in DMF within 2-5 min at room temperature, followed by desulfurization under UV light for 1-2 h in the presence of TCEP·HCl. The method was then used to synthesize 2-deoxy glycosides with absolute α/β-configuration via stereoselective control of C-2 thioacetate in glycosylation. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/31310551/A_One-Pot_Method_for_Removal_of_Thioacetyl_Group_via_Desulfurization_under_Ultraviolet_Light_To_Synthesize_Deoxyglycosides L2 - https://dx.doi.org/10.1021/acs.orglett.9b02033 DB - PRIME DP - Unbound Medicine ER -