(2-Benzyloxyphenyl)acetyl (BnPAc): A Participating Relay Protecting Group for Diastereoselective Glycosylation and the Synthesis of 1,2-trans Glycosyl Esters
Autor: | Julia Weber, Christian Hametner, Theresa Schwarz, Hannes Mikula, Simon Krauter |
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Rok vydání: | 2018 |
Předmět: | |
Zdroj: | Synlett. 29:2265-2268 |
ISSN: | 1437-2096 0936-5214 |
DOI: | 10.1055/s-0037-1610255 |
Popis: | 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/H2 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. |
Databáze: | OpenAIRE |
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