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Mild Oxidative Cleavage of 9-BBN-Protected Amino Acid Derivatives
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Physical Organic Chemistry.
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Physical Organic Chemistry.
2015 (English)In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 17, 3767-3770 p.Article in journal (Refereed) Published
Abstract [en]

Protection of the amino acid moiety using 9-BBN is an effective method to enable side chain manipulations in synthesis of complex amino acids. We investigated the standard, mild method for deprotection of the 9-BBN group in methanolic chloroform, and found that it relies on a slow oxidation mediated by molecular oxygen. Building on this insight, we have developed a method that allows for a fast and selective deprotection using simple peroxy acid reagents. After Fmoc protection, products were isolated in >90% yield for a series of amino acid derivatives, including a galactosylated derivative of hydroxylysine.

Place, publisher, year, edition, pages
2015. no 17, 3767-3770 p.
Keyword [en]
Amino acids, Protecting groups, Oxidation
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:uu:diva-257008DOI: 10.1002/ejoc.201500361ISI: 000355534600016OAI: oai:DiVA.org:uu-257008DiVA: diva2:828091
Available from: 2015-06-29 Created: 2015-06-29 Last updated: 2017-12-04Bibliographically approved

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Ankner, TobiasKihlberg, Jan

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