The selection of a protective group and protection strategy are important components of synthetic methodology always where the chemical reaction must be carried out selectively at one reaction side in a multifunctional compound, than other side requires to be temporarily blocked. In the case of natural compound like carbohydrates, nucleosides or steroids, functional groups are hydroxyls and amines, which necessities regioselective protection strategies. Etherification is one of the most fundamental and most frequently used important reaction in synthetic carbohydrates chemistry¹. Protection of a hydroxyl functionality as the methoxybenzyl ethers is preferred as a temporary protective group when neutral condition of deprotection are required. Additionally this type of protective group in contrast to ester, acetal and silyl protective groups, do not undergo unwanted migration between neighboring functional groups. The metoxybenzyl protection of carbohydrates was already reported in literature with application of different strategies and conditions. Despite that, the search for new efficient etherification method is still a matter of general interest^2,3.

In this communication we report the novel method protection of hydroxyl and amine functionality with p-methoxybenzyl, 2,4-dimethoxybenzyl and 3,4-dimethoxybenzyl groups using methoxybenzyl N-allyl thiocarbamates as donors protective groups. These compounds are readily obtained from methoxybenzyl alcohols by reaction with commercially available N-allyl isothiocyanate⁴.

Acknowledgement

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

References

1) Green, T.; Wuts, P. Protective Groups in Organic Synthesis, 2^nd ed.: John Wiley and Sons: New York, 1997, 2) Levy, D. E.; Fϋgelli, P. The Organic Chemistry of Sugars, Taylor Francis Group LLC: New York, 2006, 3) Hanessian, S.; Preparative carbohydrate chemistry, Marcel DEKKER; New York, 1996, 4) Kasprzycka A. and Szeja W. Polish J. Chem. 2005, 79, 329-333.

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