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. 2017 Apr 7;82(7):3926-3934.
doi: 10.1021/acs.joc.7b00065. Epub 2017 Mar 27.

Mild Method for 2-Naphthylmethyl Ether Protecting Group Removal Using a Combination of 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) and β-Pinene

Dina Lloyd  1 , Marissa Bylsma  1 , Danielle K Bright  1 , Xizhao Chen  1 , Clay S Bennett  1
Affiliations

Mild Method for 2-Naphthylmethyl Ether Protecting Group Removal Using a Combination of 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) and β-Pinene

Dina Lloyd et al. J Org Chem. .

Abstract

The use of a combination of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) and β-pinene permits the removal of 2-naphthylmethyl (Nap) ether protecting groups on highly sensitive substrates. The reaction tolerates both acid and base sensitive protecting groups, and products are afforded in 68-96% yield. The utility of the method is demonstrated by the removal of the Nap protecting groups on highly sensitive 2,6-dideoxy-sugar disaccharides.

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Scheme 1
Scheme 1. Synthesis of Substrates Used in this Study
Scheme 2
Scheme 2. Identification of Byproduct from the Reaction of 17 without β-Pinene
See this image and copyright information in PMC

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