70008-07-0Relevant articles and documents
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.