To study the effect of exchanging an O-for a S-glycosidic linkage on the chemical and biological properties of Fdx derivatives, we envisaged the synthesis of S-Fdx from 1thionoviose. Noviose is not commercially available. However, the by-product of the LAmediated reaction of Fdx with thiols is the noviose moiety that is cleaved off from the natural product (Fig. , Fig. ). Isolation of the 4-O-isobutyryl noviose 7 from the aqueous phase, followed by acetylation, afforded the per-O-acylated noviose 8 as a mixture of anomers (α:β = 1:2). The acylated pyranose 8 was then re-used to access the 1-thiosugar, analogous to previously reported strategies. Noteworthy, the intermediately formed glycosyl bromide proved to be highly air and moisture sensitive. Due to the limited stability, the freshly prepared noviosyl bromide was directly treated with thiourea, followed by reduction by sodium metabisulfite to provide the per-O-acylated 1-thionoviose 9 in a yield of 50% (over 3 steps) as an inseparable anomeric mixture (α:β = 10:6). The mixture was subjected to SnCl4 mediated epimerization to provide 1-b-thionoviose. While re-using the noviose by-product presents an elegant strategy to access 1-thionoviose derivatives, orthogonal protecting groups are necessary to selectively free the syn-diol leaving the 4-O-isobutyrate intact.