- Simple and efficient synthesis of 2,5-anhydro-d-glucitol
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The synthesis of 2,5-anhydro-d-glucitol is described via intramolecular cyclization of diepoxide using ammonium formate in MeOH by a microwave-assisted reaction. The overall yield was 32% from d-mannitol derivative involving seven steps.
- Arag?o-Leoneti, Valquiria,Carvalho, Ivone
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p. 1087 - 1089
(2013/04/10)
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- A general oxidative cyclization of 1,5-dienes using catalytic osmium tetroxide
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Dihydroxylation of 1,5-dienes under acidic conditions is sufficient to induce an efficient oxidative cyclization that produces stereochemically defined tetrahydrofurans in one step [Eq. (1)]. This method is very general and efficient for a range of dienes
- Donohoe, Timothy J.,Butterworth, Sam
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p. 948 - 951
(2007/10/03)
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- Preparation of 2,5-anhydrohexitols (part I). Silicon-directed stereocontrolled cyclization
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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.
- Van Delft, Floris L.,Valentijn, A. Rob P.M.,Van Der Marel, Gijs A.,Van Boom, Jacques H.
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p. 165 - 190
(2007/10/03)
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