(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
Rok vydání:	2018
Předmět:	chemistry.chemical_classification Glycosylation 010405 organic chemistry Stereochemistry Organic Chemistry Glycoside 010402 general chemistry 01 natural sciences 0104 chemical sciences chemistry.chemical_compound chemistry Group (periodic table) Glycosyl Protecting group
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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