70008-07-0Relevant academic research and scientific papers
1,6-CYCLIZATION REACTIONS OF SELECTED ALDOHEXOPYRANOSES via THEIR 1-O-TOSYL DERIVATIVES
Wisniewski, Andrzej,Madaj, Janusz,Skorupowa, Eugenia,Sokolowski, Janusz
, p. 873 - 880 (2007/10/02)
2,3,4,6-Tetra-O-acetyl-D-gluco-, D-galacto- and D-mannopyranoses were tosylated with p-tolenesulfonyl chloride to afford their 1-O-tosyl derivatives which were cyclized "in situ" in a methanolic solution of sodium methoxide. 1,6-Cyclization products were obtained only with D-glucose and D-galactose derivatives.Cyclization of derivatives of D-glucose i.e. 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl chloride, 3,4,6-tri-O-acetyl-1,2-anhydro-α-D-glucopyranose (Brigl's anhydride) and 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide enabled the estimation of the influence of configuration at C-1 and C-2 on the course of cyclization.All product mixtures were separated by capillary gas chromatography (CGC) and their components were identified by coinjection with standards.
Sugar Tosylates via p-Toluenesulfinic Acid Esters. - p-Toluenesulfinimidazolide - A Reagent for Formation of Sulfinic Acid Esters without Using Halides
Redlich, Hartmut,Meyer, Wolf-Ulrich
, p. 1354 - 1360 (2007/10/02)
The reaction of the protected sugar derivatives 1, 4, 7, 10, 13, 16, 19 and 20 with p-toluenesulfinimidazolide prepared from p-toluenesulfinic acid and N,N'-carbonyldiimidazole yields the corresponding p-toluenesulfinic esters 2, 5, 8, 11, 14, 17, 20 and 22.With the exception of 20 and 22, these products can be oxidized with m-chloroperbenzoic acid in high yields and short overall reaction times to the tosylates 3, 6, 9, 12, 15 and 18.
