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Gewählte Publikation:

Weber, J; Krauter, S; Schwarz, T; Hametner, C; Mikula, H.
(2018): (2-Benzyloxyphenyl)acetyl (BnPAc): A Participating Relay Protecting Group for Diastereoselective Glycosylation and the Synthesis of 1,2-trans Glycosyl Esters
SYNLETT. 2018; 29(17): 2265-2268. FullText FullText_BOKU

The (2-benzyloxyphenyl) acetyl group has been identified as a new protecting group for hydroxyl functions. Various alcohols could be easily protected with high yields, and deprotection was achieved by a relay approach using Pd/H-2 in combination with 1,8-bis(dimethylamino) naphthalene, conditions that are orthogonal to ester groups. The new protecting group is stable in glycosylation reactions demonstrating an effective neighboring group participation leading to the exclusive formation of 1,2-trans glycosides and glycosyl esters.
Autor*innen der BOKU Wien:
Krauter Simon

Find related publications in this database (Keywords)
protecting groups
relay deprotection
neighboring group participation
anchimeric assistance
glycosyl esters

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