An Improved Protocol for the Stereoselective Synthesis of ß-d-Glycosyl Fluorides from 2-O-Acyl Thioglycosides.
J Org Chem
; 87(21): 14230-14240, 2022 11 04.
Article
em En
| MEDLINE
| ID: mdl-36222442
ABSTRACT
A safe and operationally simple protocol for the preparation of ß-d-glycosyl fluorides is presented. We demonstrate that a precise combination of XtalFluor-M, N-bromosuccinimide, and Et3N·3HF can mediate facile, high-yielding, and diastereoselective conversions of 2-O-acyl thioglycosides to ß-d- and other 1,2-trans glycosyl fluorides. The key roles of these reagents are dissected in this work, as is the impact of their interplay on the fluorination stereoselectivity.
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1
Base de dados:
MEDLINE
Assunto principal:
Tioglicosídeos
Idioma:
En
Ano de publicação:
2022
Tipo de documento:
Article