It could be expected that the sulfinylation of the hydroxyl group(s) of a sugar moiety should influence its biological activity. This type of sugar functionalization generate simultaneously interesting diastereomeric O-sulfinates, which can be used as substrates for the synthesis of enantiomerically pure sulfinyl derivatives^[1]. To verify experimentally both assumptions we decided to check whether the reactions of organometallic reagents with diastereomerically pure (R)-1,2-O-isopropylidene-3,5-O-sulfinyl-a-D-glucofuranose^[2] or the sulfite derived from 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (DAG) could be stopped at the stage of the corresponding sulfinates.

In this paper the influence of the reaction conditions on the reaction outcome with sterically demanding organometallics and an X-ray structural analysis of t-butanesulfinate derived from (R)-1,2-O-isopropylidene-3,5-O-sulfinyl-a-D-glucofuranose will be discussed and experimental details will be presented

Acknowledgment:

This work was supported by the network "Synthesis, structure and therapeutic properties of compounds and organic substances".

References:

[1] J. Drabowicz, D. Krasowska, A. Zając, Speciality Chemicals Magazine, 2007, 27 34-37 and references therein

[2] Borsuk, K.; Frelek, J.; Łysek, R.; Urbańczyk-Lipkowska, Z.; Chmielewski, M., Chirality 2001, 13, 533-540.

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