title: 9-BBN: An amino acid protecting group for functionalization of amino acid side chains in organic solvents.
abstract: 9-Borabicyclononane (9-BBN) has been utilized to protect functionalized amino acids for potential chemoselective side chain manipulation. The 9-BBN group imparts organic solubility to otherwise hydrophilic molecules and is tolerant of a wide range of reaction conditions. The high degree of solubility of these molecules in THF is particularly noteworthy. It is cleaved with either aqueous HCl or by exchange with ethylenediamine in methanol. [reaction: see text]
authors.affiliation: Discovery Research, Dow AgroSciences LLC, 9330 Zionsville Road, Indianapolis, IN 46268-1054, USA..
authors.forename: William H
authors.initials: WH
authors.lastname: Dent
authors.forename: W Randal
authors.initials: WR
authors.lastname: Erickson
authors.forename: Stephen C
authors.initials: SC
authors.lastname: Fields
authors.forename: Marshall H
authors.initials: MH
authors.lastname: Parker
authors.forename: Eric G
authors.initials: EG
authors.lastname: Tromiczak
mesh_terms: D000596:Amino Acids / Q000737:chemistry*; D001896:Boron Compounds / Q000737:chemistry; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000737:chemistry; D007202:Indicators and Reagents; D009952:Ornithine / Q000031:analogs & derivatives / Q000737:chemistry; D012995:Solubility; D012997:Solvents
chemical_list: D000596:Amino Acids; D001896:Boron Compounds; D019086:Bridged Bicyclo Compounds, Heterocyclic; D007202:Indicators and Reagents; D012997:Solvents; C454803:9-borabicyclononane; D009952:Ornithine