Mild method for the synthesis of α-glycosyl chlorides: A convenient protocol for quick one-pot glycosylation

Carbohydr Res. 2023 Oct 20;534:108976. doi: 10.1016/j.carres.2023.108976. Online ahead of print.ABSTRACTA simple and efficient protocol for the preparation of α-glycosyl chlorides within 15-30 min is described which employs a stable, cheap, and commercially available Trichloroisocyanuric acid (TCCA) as non-toxic chlorinating agent along with PPh3. This process involved a wide range of substrate scope and is well-suited with labile hydroxyl protecting groups such as benzyl, acetyl, benzoyl, isopropylidene, benzylidene, and TBDPS (tert-butyldiphenylsilyl) groups. This process is operationally simple, mild conditions and obtained good yields with excellent α selectivity. Moreover, a multi-catalyst one-pot glycosylation can be carried out to transform the glycosyl hemiacetals directly to a various O-glycosides in high overall yields without the need for separation or purification of the α-glycosyl chloride donors.PMID:37871478 | DOI:10.1016/j.carres.2023.108976
Source: Carbohydrate Research - Category: Genetics & Stem Cells Authors: Source Type: research