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; Marissa Bylsma; Danielle K Bright; Xizhao Chen; Clay S Bennett

doi:10.1021/acs.joc.7b00065

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

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

Authors

Dina Lloyd¹, Marissa Bylsma¹, Danielle K Bright¹, Xizhao Chen¹, Clay S Bennett¹

Affiliation

¹ Department of Chemistry, Tufts University , Medford, Massachusetts 02155, United States.

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.

Publication types

Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't

MeSH terms

Benzoquinones / chemistry*
Bicyclic Monoterpenes
Bridged Bicyclo Compounds / chemistry*
Ethers / chemistry*
Monoterpenes / chemistry*
Spectrum Analysis / methods

Substances

Benzoquinones
Bicyclic Monoterpenes
Bridged Bicyclo Compounds
Ethers
Monoterpenes
dichlorodicyanobenzoquinone
beta-pinene

Grants and funding

R01 GM115779/GM/NIGMS NIH HHS/United States