2,3-Dicyclohexylsuccinimide as a directing/protecting group for the regioselective glycosylation or alkylation of purines

Ayan Pal; Kerry J. Salandria; Joseph W. Arico; Mark K. Schlegel; Larry W. McLaughlin

doi:10.1039/C3CC37265K

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2,3-Dicyclohexylsuccinimide as a directing/protecting group for the regioselective glycosylation or alkylation of purines†

Ayan Pal,^a Kerry J. Salandria,^a Joseph W. Arico,^a Mark K. Schlegel*^a and Larry W. McLaughlin*^a

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* Corresponding authors

^a Boston College, Department of Chemistry, Merkert Chemistry Center, 2609 Beacon Street, MA 02467, Chestnut Hill, USA
E-mail: larry.mclaughlin@bc.edu, mark.schlegel@bc.edu
Fax: +001 617 552 2705
Tel: +001 617 552 3622

Abstract

Here we describe the synthesis and application of a novel 2,3-dicyclohexylsuccinimide (Cy₂SI) protecting group towards regioselective purine glycosylation and alkylation reactions. This bulky protecting group promotes high regioselectivity during the glycosylation (as well as diastereoselectivity) or alkylation of purines using Hoffer's chlorosugar or tert-butyl bromoacetate, respectively. Cy₂SI offers the additional synthetic advantage that other base-labile protecting groups, such as toluoyl esters, can be selectively removed in its presence without affecting the imide.

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DOI: https://doi.org/10.1039/C3CC37265K
Article type: Communication
Submitted: 04 Oct 2012
Accepted: 25 Feb 2013
First published: 25 Feb 2013

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Chem. Commun., 2013,49, 2936-2938

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2,3-Dicyclohexylsuccinimide as a directing/protecting group for the regioselective glycosylation or alkylation of purines

A. Pal, K. J. Salandria, J. W. Arico, M. K. Schlegel and L. W. McLaughlin, Chem. Commun., 2013, 49, 2936 DOI: 10.1039/C3CC37265K

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Chemical Communications

2,3-Dicyclohexylsuccinimide as a directing/protecting group for the regioselective glycosylation or alkylation of purines†

Abstract

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2,3-Dicyclohexylsuccinimide as a directing/protecting group for the regioselective glycosylation or alkylation of purines

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