Synthesis of deoxy derivatives of glucosinolates glucotropaeolin and glucobrassicin

Article abstract of DOI:10.1016/0008-6215(95)00265-0

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.Keywords: Glucosinolates; Glucotropaeolin; Glucobrassicin; 1-Thioglucopyranose; Deoxy derivatives