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TitleThe dimethoxyphenylbenzyl protecting group: An alternative to the p-methoxybenzyl group for protection of carbohydrates
Publication TypeJournal Article
Year of Publication2013
AuthorsRankin, G.M., Maxwell-Cameron I., Painter G.F., and Larsen D.S.
JournalJournal of Organic Chemistry
Volume78
Issue11
Pagination5264 - 5272
Date Published2013
ISSN00223263 (ISSN)
KeywordsAcidic conditions, acidity, Alcohols, article, Benzyl Compounds, benzyl derivative, Benzyl ethers, carbohydrate derivative, Carbohydrates, degradation, deprotection reaction, ester derivative, ether derivative, Ethers, glycoside, Glycosidic linkages, High yield, Molecular Structure, P-methoxybenzyl, Protecting group, Reaction conditions, Reagent systems, toluene derivative
AbstractA reliable reagent system for the cleavage of 4-(3,4-dimethoxyphenyl)benzyl (DMPBn) ethers under acidic conditions has been established. Treatment of DMPBn-protected mono- and pseudodisaccharides with TFA in anhydrous CH 2Cl2 and 3,4-(methylenedioxy)toluene as a cation scavenger resulted in the selective cleavage of the DMPBn ether giving the corresponding deprotected products in moderate to high yields. Examples are reported which show that allyl, benzyl, and p-bromobenzyl ethers, esters, and glycosidic linkages are stable to these reaction conditions. The selective cleavage of allyl, p-bromobenzyl, and PMB ethers in protected carbohydrates containing DMPBn ethers are also demonstrated. This work establishes the 4-(3,4-dimethoxyphenyl) benzyl ether as an effective and robust alternative to p-methoxybenzyl as a protecting group for alcohols. © 2013 American Chemical Society.
URLhttp://www.scopus.com/inward/record.url?eid=2-s2.0-84879313994&partnerID=40&md5=ab83062195a2ad42bf0a9bebd8d42547
DOI10.1021/jo4004184

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