The synthesis of complex molecules, e.g., natural products, is still a challenge despite tremendous progress in organic synthesis achieved over the last decade’s [1]. Most of multistep syntheses still require many protection and deprotection procedures. In response to the increasing complexity of the molecular structures synthesized, numerous protecting groups have been developed, as well as methods for their introduction and their deprotection [2-4]. Nevertheless, new and more selective protecting groups are still required [5] while milder and more selective conditions are actively pursued [11-14]. The benzyl group like 4-methoxybenzyl (PMB), 3,4-dimethoxybenzyl (DMB), 4-nitrobenzyl and others  has been used extensively as a protecting group in carbohydrate chemistry. Benzyl ethers are frequently used as protecting groups indispensable to the general pursuit of oligosaccharides. Traditionally, preparation of arylmethyl ethers from alcohols is accomplished by Williamson ether synthesis protocol under basic conditions, by treating substrate with benzyl halide and a strong base, such as potassium hydroxide [1-8].

In this communication we report the novel method protection of sugars as the corresponding 4-methoxybenzyl, 2,4-dimethoxybenzyl and 3,4-dimethoxybenzyl  and other aryl groups using N-phenyl thionocarbamates as donors protective groups. These compounds are readily obtained from corresponding alcohols by reaction with commercially available N-phenyl isothiocyanate [9].

Acknowledgement :

Research studies part-financed by the European Union within the European Regional Development Fund (POIG.01.01.02-14-102/09).

 References:

1. Nicolaou, K. C.; Chen,  J. S. Classics in Total Synthesis III; Wiley-VCH: Weinheim 2010.
2. Kocienski, P. J. In Protecting groups; 3rd Ed.; Thieme, G. New York, 2004; pp 241-269.
3. Greene, T. W.; Wuts, P. G. M. In Protective Groups in Organic Synthesis; 3rd ed.; J. Wiley & Sons: New York, 1999; pp 5-15 and pp 120-135.
4. Blanc, A.; Bochet, C. G. In CRC Handbook of Organic Photochemistry and Photobiology; 3rd Ed.; Taylor & Francis: New York, 2012; pp 73−93.
5. Hibino, H.; Nishiuchi, Y. Org. Lett. 2012, 7, 1926.
6. Muranaka, K.; Ichikawa, S.; Matsuda, A. J. Org. Chem. 2011, 76, 9278.
7. Liang, H.; Hu, L.; Corey, E. J. Org. Lett. 2011, 13, 4120.
8. Bröhmer, M. C.; Mundinger, S.; Bräse, S.; Bannwarth, W. Angew. Chem., Int. Ed. 2011, 50, 6175.
9.  Kasprzycka A., Szeja W., Polish J. Chem., 2005, 79, 329-333.  

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