title: 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.
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.
authors.affiliation: Department of Chemistry, Tufts University , Medford, Massachusetts 02155, United States.
authors.forename: Dina
authors.initials: D
authors.lastname: Lloyd
authors.affiliation: Department of Chemistry, Tufts University , Medford, Massachusetts 02155, United States.
authors.forename: Marissa
authors.initials: M
authors.lastname: Bylsma
authors.affiliation: Department of Chemistry, Tufts University , Medford, Massachusetts 02155, United States.
authors.forename: Danielle K
authors.initials: DK
authors.lastname: Bright
authors.affiliation: Department of Chemistry, Tufts University , Medford, Massachusetts 02155, United States.
authors.forename: Xizhao
authors.initials: X
authors.lastname: Chen
authors.affiliation: Department of Chemistry, Tufts University , Medford, Massachusetts 02155, United States.
authors.forename: Clay S
authors.identifier: 0000-0001-8070-4988
authors.initials: CS
authors.lastname: Bennett
mesh_terms: D016227:Benzoquinones / Q000737:chemistry*; D000081008:Bicyclic Monoterpenes; D001643:Bridged Bicyclo Compounds / Q000737:chemistry*; D004987:Ethers / Q000737:chemistry*; D039821:Monoterpenes / Q000737:chemistry*; D013057:Spectrum Analysis / Q000379:methods
chemical_list: D016227:Benzoquinones; D000081008:Bicyclic Monoterpenes; D001643:Bridged Bicyclo Compounds; D004987:Ethers; D039821:Monoterpenes; C000928:dichlorodicyanobenzoquinone; C010789:beta-pinene