ABSTRACT
1,5-Anhydro-2-deoxy-arabino-hex-1-enitols, such as the title compound, are versatile intermediates for the synthesis of a number of 2,6-dideoxy sugars commonly found in natural products. 1 Part of their utility stems from the fact that they can be used directly in synthesis 2 or converted into deoxy sugar hemiacetal donors 3 for highly stereoselective glycosylation reactions. 4 A number of methods for the preparation of these molecules have been described in the literature, which typically involve converting the C–6 oxygen of d-glucal into either a sulfonate ester or a halide, followed by reduction. 5,6 Although powerful, these approaches suffer from limitations that become apparent on a larger scale. In the case of the sulfonate ester approach, reduction is typically carried out with an excess of LiAlH4, which has been reported to be problematic on scale-up. 7 Alternatively, the sulfonate ester can be converted to a bromide or iodide, for radical dehalogenation. This latter approach adds a step to the synthetic sequence, and typically requires the use of stoichiometric amounts of highly toxic trialkyltin hydrides, which could be avoided using less-toxic alternatives. 8
