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Issue 16, 2018
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1,4-Dithiothreitol mediated cleavage of the acetal and ketal type of diol protecting groups

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Abstract

The use of 1,4-dithiothreitol (DTT) as an acetal or ketal exchange reagent and camphorsulfonic acid (CSA) as a catalyst permitted the efficient removal of benzylidene acetal and isopropylidene ketal protecting groups under mild conditions. A variety of acetal and ketal protected carbohydrates were deprotected with this method in 78–98% yields. In addition, terminal isopropylidene ketal or benzylidene acetal was selectively cleaved in the presence of internal isopropylidene ketal. Moreover, it was found that an unusual seven-membered 1,3-dithiepane was formed during the deprotection of benzylidene acetal with DTT.

Graphical abstract: 1,4-Dithiothreitol mediated cleavage of the acetal and ketal type of diol protecting groups

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Publication details

The article was received on 07 Mar 2018, accepted on 26 Mar 2018 and first published on 27 Mar 2018


Article type: Research Article
DOI: 10.1039/C8QO00247A
Citation: Org. Chem. Front., 2018,5, 2427-2431
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    1,4-Dithiothreitol mediated cleavage of the acetal and ketal type of diol protecting groups

    Y. Liu, J. Zeng, J. Sun, L. Cai, Y. Zhao, J. Fang, B. Hu, P. Shu, L. Meng and Q. Wan, Org. Chem. Front., 2018, 5, 2427
    DOI: 10.1039/C8QO00247A

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