Synlett 2018; 29(17): 2265-2268
DOI: 10.1055/s-0037-1610255
letter
© Georg Thieme Verlag Stuttgart · New York

(2-Benzyloxyphenyl)acetyl (BnPAc): A Participating Relay Protecting Group for Diastereoselective Glycosylation and the Synthesis of 1,2-trans Glycosyl Esters

Julia Weber
a   Institute of Applied Synthetic Chemistry Vienna University of Technology (TU Wien), Getreidemarkt 9, 1060 Vienna, Austria   Email: hannes.mikula@tuwien.ac.at
,
Simon Krauter
a   Institute of Applied Synthetic Chemistry Vienna University of Technology (TU Wien), Getreidemarkt 9, 1060 Vienna, Austria   Email: hannes.mikula@tuwien.ac.at
b   Division of Organic Chemistry, University of Natural Resources and Life Sciences, Vienna (BOKU), Muthgasse 18, 1190 Vienna, Austria
,
Theresa Schwarz
a   Institute of Applied Synthetic Chemistry Vienna University of Technology (TU Wien), Getreidemarkt 9, 1060 Vienna, Austria   Email: hannes.mikula@tuwien.ac.at
,
Christian Hametner
a   Institute of Applied Synthetic Chemistry Vienna University of Technology (TU Wien), Getreidemarkt 9, 1060 Vienna, Austria   Email: hannes.mikula@tuwien.ac.at
,
a   Institute of Applied Synthetic Chemistry Vienna University of Technology (TU Wien), Getreidemarkt 9, 1060 Vienna, Austria   Email: hannes.mikula@tuwien.ac.at
› Author Affiliations
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)


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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.

Supporting Information