Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml
Synlett 2018; 29(17): 2265-2268
DOI: 10.1055/s-0037-1610255
DOI: 10.1055/s-0037-1610255
letter
(2-Benzyloxyphenyl)acetyl (BnPAc): A Participating Relay Protecting Group for Diastereoselective Glycosylation and the Synthesis of 1,2-trans Glycosyl Esters
We thank the Austrian Research Promotion Agency (FFG, BRIDGE-Project 843488) for financial support.Further Information
Publication History
Received: 19 June 2018
Accepted after revision: 20 July 2018
Publication Date:
06 September 2018 (online)


Abstract
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.
Key words
protecting groups - relay deprotection - neighboring group participation - anchimeric assistance - glycosides - glycosyl estersSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610255.
- Supporting Information