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

ABSTRACT: The use of a combination of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) and ?-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.

SUBMITTER: Lloyd D

PROVIDER: S-EPMC5387675 | biostudies-literature | 2017 Apr

REPOSITORIES: biostudies-literature

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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.

Lloyd Dina D Bylsma Marissa M Bright Danielle K DK Chen Xizhao X Bennett Clay S CS

The Journal of organic chemistry 20170327 7

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. ...[more]

PMID: 28281755

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