Synthesis of deoxy derivatives of the glucosinolates glucotropaeolin and glucobrassicin

The syntheses of 3,4,6-tri-O-acetyl-2-deoxy-1-thio-d-arabino-hexopyranose, 2,4,6-tri-O-acetyl-3-deoxy-1-thio-β-d-ribo-hexopyranose, 2,3,6-tri-O-benzoyl-4-deoxy-1-thio-β-d-xylo-hexopyranose, and 2,3,4-tri-O-acetyl-6-deoxy-1-thio-β-d-glucopyranose are reported. These thiols were coupled with phenylacetohydroximoyl chloride or indol-3-ylacetohydroximoyl chloride, respectively. Sulfation and subsequent deprotection yielded the corresponding deoxy derivatives of glucotropaeolin and glucobrassicin, two major representatives of the glucosinolate family.