196951-56-1Relevant articles and documents
Thioglycosides of N-acetyl- and N-glycolylneuraminic acids as glycosyl donors. Synthesis of 3-aminopropylglycosides
Simeoni,Tuzikov,Byramova,Bovin
, p. 126 - 132 (2007/10/03)
Protected derivatives of ethylthioglycosides of N-acetyl- and N-glycolylneuraminic acids were shown to be efficient glycosyl donors in the reaction with 3-trifluoroacetamidopropanol promoted with a N-iodosuccinimide-trifluoromethanesulfonic acid (or its trimethylsilyl ester) pair. This reaction led to high yields of the corresponding anomeric glycosides; however, its α-stereoselectivity was only moderate: α: β ratio ranged from 1 : 1 to 2 : 1. An analog of the Neu5Gc-donor with the O9 and O4 acetyl groups substituted by acetoxyacetyl groups manifested a high tendency to the predominant formation of the α-anomer. Separation of the anomers and their deprotection prepared the corresponding aminopropylglycosides for further condensation with a polymer carrier.
