222408-64-2

Upstream product

• 1941-50-0 D-arabinose diethyl dithioacetal 
• 175606-34-5 2,3-di-O-benzyl-4,5-O-isopropylidene-D-arabinose diethyl dithioacetal 
• 70337-25-6 4,5-O-isopropylidene-D-arabinose diethyldithioacetal 
• 106929-09-3 (2S,3R,4R)-2,3-dibenzyloxy-4,5-isopropylidenedioxypentanal 
• 100-39-0 benzyl bromide 
• 222408-63-1 3,4-di-O-benzyl-1-deoxy-1-dimethylphenylsilyl-5,6-O-isopropylidene-D-glucitol 

Downstream Products

• 222555-96-6 2,5-anhydro-3,4-di-O-benzyl-D-mannitol 
• 129115-89-5 3,4-dibenzyloxy-2,5-dihydroxymethyltetrahydrofuran 
• 41107-82-8 2,5-anhydro-D-mannitol 
• 222408-65-3 2,5-anhydro-3,4-di-O-benzyl-1-deoxy-1-dimethylphenylsilyl-D-glucitol 
• 222408-66-4 2,5-anhydro-3,4-di-O-benzyl-1-deoxy-1-dimethylphenylsilyl-D-mannitol 

Relevant academic research and scientific papers

Preparation of 2,5-anhydrohexitols (part I). Silicon-directed stereocontrolled cyclization

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.