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A simple, mild, and inexpensive catalytic system consisting of 1,8-diazabicyclo[5. Wang, K. Kodama and T. Hirose, Catal. To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

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A regioselective reductive ring opening of benzylidene acetals in carbohydrate derivatives using triethylsilane and molecular iodine is fast and compatible with most of the functional groups encountered in oligosaccharide synthesis, and offers excellent yields. The reaction conditions are equally effective in thioglycosides. Panchadhayee, A. Misra, Synlett , , In situ generation of molecular hydrogen by addition of triethylsilane to palladium on charcoal results in rapid and efficient reduction of multiple bonds, azides, imines, and nitro groups, as well as deprotection of benzyl and allyl groups under mild, neutral conditions.

Mandal, J. McMurray, J. Transfer hydrogenation utilizing palladium on carbon and formic acid provides a fast and simple removal of O -benzyl groups from carbohydrate derivatives. However, when formic acid is the hydrogen donor, a large amount of palladium has to be used.

Bieg, W. Szeja, Synthesis , , An efficient and convenient method allows the removal of benzyl ether protecting groups in the presence of other functionality.

Varying the solvent allows the removal of trityl groups in the presence of benzyl ethers. Congreve, E. Davison, M. Fuhry, A. Holmes, A. Payne, R. Robinson, S. Ward, Synlett , , A chemoselective debenzylation of aryl benzyl ethers proceeds at low temperature with a combination of BCl 3 and pentamethylbenzene as a cation scavenger in the presence of various functional groups.

Okano, K. Okuyama, T. Fukuyama, H. Tokuyama, Synlett , , The reaction of different protected alcohols, amines and amides with lithium and a catalytic amount of naphthalene in THF at low temperature leads to their deprotection under very mild reaction conditions, the process being in many cases chemoselective.

Alonso, D. Yus, Tetrahedron , , 53 , Benzyl ether protective groups are oxidatively removed by ozone under relatively mild conditions. Reaction products are benzoic ester, benzoic acid, and the corresponding alcohol. Subsequent deacylation with sodium methoxide affords a convenient debenzylation technique which has been applied to various O -benzyl protected carbohydrates. Angibeaud, J. Defaye, A. Gadelle, J. Utille, Synthesis , , The deprotection of benzyl ethers was effectively realized in the presence of 2,3-dichloro-5,6-dicyano- p -benzoquinone DDQ in MeCN under photoirradiation using a long wavelength UV light.

Rahim, S. Matsumura, K. Toshima, Tetrahedron Lett. Fetching data from CrossRef. This may take some time to load.

Loading related content. Jump to main content. Jump to site search. You do not have JavaScript enabled. Please enable JavaScript to access the full features of the site or access our non-JavaScript page. Issue 47, From the journal: Chemical Science. Bergmann a and M. This article is part of the themed collection: Most popular organic chemistry articles.

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