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1.
Carbohydr Res ; 541: 109167, 2024 Jul.
Article in English | MEDLINE | ID: mdl-38823063

ABSTRACT

This paper describes a mild and efficient catalytic deprotection method for isopropylidene ketals and benzylidene acetals using AcOH/H2O/DME(1,2-Dimethoxyethane). The method effectively removes ketal and acetal protecting groups from 2-deoxyglycosides which are prone to hydrolysis under acidic conditions. Moreover, it enables the selective removal of the terminal ketal over an internal one.


Subject(s)
Glycosides , Glycosides/chemistry , Glycosides/chemical synthesis , Water/chemistry , Stereoisomerism , Ketones/chemistry , Catalysis , Acetals/chemistry , Molecular Structure
2.
Chem Commun (Camb) ; 2024 Jun 26.
Article in English | MEDLINE | ID: mdl-38919041

ABSTRACT

This paper shows a novel oxidative functionalization of α-amino ketones to yield the corresponding α-ketoamides and α-acylimidates. The reaction proceeds via oxygen delivery from water/alcohols in conjunction with an electron acceptor and 4-dimethylaminopyridine (DMAP). Mechanistic study indicates that DMAP exhibits a dual function of nucleophilic catalysis and proton abstraction.

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