1, 6-Anhydro-1-thio-β-D-glucopyranose (Thiolevoglucosan) and the Corresponding Sulfoxides and Sulfone

…, J Poláková, M Hamerníková, I Císařová…

文献索引：Budesinsky, Milos; Polakova, Jana; Hamernikova, Michaela; Cisarova, Ivana; Trnka, Tomas; Cerny, Miloslav Collection of Czechoslovak Chemical Communications, 2006 , vol. 71, # 3 p. 311 - 336

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被引用次数: 5

摘要

Abstract Starting 1, 2, 3, 4-tetra-O-acetyl-6-O-tosyl-β-D-glucopyranose (3) was converted into 2, 3, 4-tri-O-acetyl-1-thio-6-O-tosyl-β-D-glucopyranose (6) via intermediate glycosyl bromide 4 and S-thiouronium salt 5. Treatment of compound 6 with sodium methoxide gave 1, 6- anhydro-1-thio-β-D-glucopyranose (thiolevoglucosan 2a). The isomeric sulfoxides 7 and 8 were prepared by selective oxidation of thiolevoglucosan 2a with hydrogen peroxide or 3- ...