On the electron withdrawing nature of ethers in glycosylation chemistry
Mikkel H S Marqvorsen1, Anne Brinkø2, Henrik H Jensen2
1Department of Biomedicine, Aarhus University, Høegh-Guldbergs Gade 10, 8000, Aarhus C, Denmark.
Abstract:
The present paper is a commentary on the electronic effects that protecting groups exert on glycosylation chemistry. Specifically, its purpose is to rectify the misguided use of the term electron donating benzyl groups, which hardly makes sense in the context of protecting groups on alcohols in saturated systems such as carbohydrates. It is argued that benzyl ethers (OBn) should rightfully be referred to as being inductively electron withdrawing, even if they are less so than benzoyl esters (OBz).
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