Benzene-1,3-disulfonyl Fluoride Mediated Synthesis of Glycosyl Fluorides from Glycosyl Hemiacetals.
| Autor: | Dey S; Department of Chemistry, Indian Institute of Technology Hyderabad, Kandi-502 284, Sangareddy, Telangana, India., Dwivedi S; Department of Chemistry, Indian Institute of Technology Hyderabad, Kandi-502 284, Sangareddy, Telangana, India., Giri D; Department of Chemistry, Indian Institute of Technology Hyderabad, Kandi-502 284, Sangareddy, Telangana, India., Sau A; Department of Chemistry, Indian Institute of Technology Hyderabad, Kandi-502 284, Sangareddy, Telangana, India. |
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| Jazyk: | angličtina |
| Zdroj: | Organic letters [Org Lett] 2024 Nov 21. Date of Electronic Publication: 2024 Nov 21. |
| DOI: | 10.1021/acs.orglett.4c03968 |
| Abstrakt: | We developed an efficient method for synthesizing glycosyl fluorides from glycosyl hemiacetals using benzene-1,3-disulfonyl fluoride ( S2 ) as the fluorinating agent in combination with the base DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) under mild conditions. This approach enabled the successful synthesis of 17 glycosyl fluorides with various functional groups, including disaccharides and deoxysulfates, with yields of up to 99%. The utility of these synthesized glycosyl fluorides was further demonstrated in the synthesis of important O - and C -glycosides. |
| Databáze: | MEDLINE |
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