Study on the fluorination of 1, 2-O-isopropylidene D-pentofuranose with DAST and its scalable application

•Scalable synthesis of rare d-lyxose.•Scalable synthesis of 3′-fluoro-3′-deoxy-β-d-ribofuranosyl-7-halogen-7-deazapurine derivative.•Inversion of configuration of d-pentofuranosides promoted by DAST reagent. The research focuses on the inversion of configuration at C3 of 1,2-O-isopropylidene-d-arabi...

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Bibliographic Details
Published in:Journal of fluorine chemistry 2023-11, Vol.272, p.110205, Article 110205
Main Authors: Liu, Chunyu, Liang, Fazhan, Chen, Yu, Pan, Xianhua, Xia, Zheng
Format: Article
Language:English
Subjects:
3-fluoro-3-deoxy-D-furanosides
7-deazapurine
D-lyxose
DAST
Scalable synthesis
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Summary:•Scalable synthesis of rare d-lyxose.•Scalable synthesis of 3′-fluoro-3′-deoxy-β-d-ribofuranosyl-7-halogen-7-deazapurine derivative.•Inversion of configuration of d-pentofuranosides promoted by DAST reagent. The research focuses on the inversion of configuration at C3 of 1,2-O-isopropylidene-d-arabinofuranoside and d-ribofuranoside promoted by DAST. Both the initial configuration and the presence of C5 acyl group in d-furanosides are the key factors for this inversion due to the formation of cyclic oxonium ion intermediates. This inversion of configuration has been successfully applied to scalable synthesis of d-lyxose and 2′,5′-di-O-benzoyl-3′-fluoro-3′-deoxy-β-d-ribofuranosyl-7-halogen-7-deazapurine. [Display omitted]
ISSN:0022-1139
1873-3328
DOI:10.1016/j.jfluchem.2023.110205