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 | Zendy

Dina Lloyd | Zendy; Marissa Bylsma | Zendy; Danielle K. Bright | Zendy; Xizhao Chen | Zendy; Clay S. Bennett | Zendy

Open Access

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

Author(s) -

Dina Lloyd,

Marissa Bylsma,

Danielle K. Bright,

Xizhao Chen,

Clay S. Bennett

Publication year - 2017

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/acs.joc.7b00065

Subject(s) - chemistry , protecting group , yield (engineering) , ether , organic chemistry , benzoquinone , nap , chromatography , materials science , alkyl , neuroscience , metallurgy , biology

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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