Tetrahedron Letters p. 9047 - 9050 (1997)
Update date:2022-09-26
Topics:
Offer, John
Johnson, Tony
Quibell, Martin
Reversible alkylation of the C-terminal amide-bond of a protected peptide segment with 2-hydroxy-4-methoxybenzyl dramatically suppresses epimerisation during activation and coupling. However, due to the formation of a 4,5-dihydro-8-methoxy-1,4-benzoxazepin-2(3H)-one species upon activation the rate of coupling is low. A safety-catch amide-bond protecting group, 6-hydroxy-5-methyl-1,3- benzoxathiolyl, has been designed to suppress epimerisation and couple with excellent yield.
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