222408-63-1Relevant academic research and scientific papers
Preparation of 2,5-anhydrohexitols (part I). Silicon-directed stereocontrolled cyclization
Van Delft, Floris L.,Valentijn, A. Rob P.M.,Van Der Marel, Gijs A.,Van Boom, Jacques H.
, p. 165 - 190 (2007/10/03)
Stereoselective chain-extension of carbohydrate aldehydes with the hydroxymethylating reagent (dimethylphenylsilyl)methylmagnesium chloride (1) followed by acid-mediated cyclization gives access to 2,5-anhydro-hexitols. The stereoselectivity of the ring closure depends on the nature of the acid, i.e., treatment with excess BF3·Et2O or catalytic H2SO4 leads to tetrahydrofurans with 2,3-cis or 2,3-trans configuration, respectively. Concomitant elimination is effectively suppressed in case of cyclisation of the more sterically hindered isopropyl substituted silanes.
Preparation of 2,5-anhydrohexitols (part II). Intramolecular nucleophilic substitution of cyclic sulfates
Van Delft, Floris L.,Valentijn, A. Rob P.M.,Van Der Marel, Gijs A.,Van Boom, Jacques H.
, p. 191 - 207 (2007/10/03)
The 2-O-acetyl-3,4-di-O-benzyl-5,6-O-cyclic sulfates 5, 16 and 25, derived from D-arabinose, D-ribose and D-xylose, respectively, are useful precursors in the synthesis of 2,5-anhydrohexitols. 5-Exo-tet cyclization of compounds 5, 16, and 25 under the inf
