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

Bennett, Clay S.

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

Version 2 2017-03-27, 21:43

Version 1 2017-03-27, 20:16

Posted on 2017-03-27 - 21:43

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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Lloyd, Dina; Bylsma, Marissa; Bright, Danielle K.; Chen, Xizhao; Bennett, Clay S. (2017). 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. ACS Publications. Collection. https://doi.org/10.1021/acs.joc.7b00065

https://doi.org/10.1021/acs.joc.7b00065

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