《Synthetic Approaches to Phosphasugars (2-oxo-1,2-oxaphosphacyclanes) Using the Anomeric Alkoxyl Radical β-Fragmentation Reaction as the Key Step》 was published in Journal of Organic Chemistry in 2020. These research results belong to Hernandez-Guerra, Daniel; Kennedy, Alan R.; Leon, Elisa I.; Martin, Angeles; Perez-Martin, Ines; Rodriguez, Maria S.; Suarez, Ernesto. Product Details of 5781-53-3 The article mentions the following:
The anomeric alkoxyl radical β-fragmentation (ARF) of carbohydrates possessing an electron-withdrawing group (EWG) at C2, promoted by PhI(OAc)2/I2, gives rise to an acyclic iodide through which a pentavalent atom of phosphorus can be introduced via the Arbuzov reaction. After selective hydrolysis and subsequent cyclization, the phosphonate or phosphinate intermediates can be converted into 2-deoxy-1-phosphahexopyranose and 2-deoxy-1-phosphapentopyranose sugars. The ARF of carbohydrates with an electron-donor group (EDG) at C2 proceeds by a radical-polar crossover mechanism, and the cyclization occurs by nucleophilic attack of a conveniently positioned phosphonate or phosphinate group to the transient oxocarbenium ion. This alternative methodol. leads to 5-phosphasugars with a 4-deoxy-5-phosphapentopyranose framework. The structure and conformation of the 2-oxo-1,2-oxaphosphinane and 2-oxo-1,2-oxaphospholane ring systems in different carbohydrate models have been studied by NMR and X-ray crystallog.Methyl 2-chloro-2-oxoacetate(cas: 5781-53-3Product Details of 5781-53-3) was used in this study.
Methyl 2-chloro-2-oxoacetate(cas: 5781-53-3) belongs to acyl chlorides. In the laboratory, acyl chlorides are generally prepared by treating carboxylic acids with thionyl chloride (SOCl2). The reaction is catalyzed by dimethylformamide and other additives.Product Details of 5781-53-3
Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics