| Title | The dimethoxyphenylbenzyl protecting group: An alternative to the p-methoxybenzyl group for protection of carbohydrates |
| Publication Type | Journal Article |
| Year of Publication | 2013 |
| Authors | Rankin, G.M., Maxwell-Cameron I., Painter G.F., and Larsen D.S. |
| Journal | Journal of Organic Chemistry |
| Volume | 78 |
| Issue | 11 |
| Pagination | 5264 - 5272 |
| Date Published | 2013 |
| ISSN | 00223263 (ISSN) |
| Keywords | Acidic 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 |
| Abstract | A 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. |
| URL | http://www.scopus.com/inward/record.url?eid=2-s2.0-84879313994&partnerID=40&md5=ab83062195a2ad42bf0a9bebd8d42547 |
| DOI | 10.1021/jo4004184 |
