175606-34-5

Upstream product

• 100-39-0 benzyl bromide 
• 70337-25-6 4,5-O-isopropylidene-D-arabinose diethyldithioacetal 
• 1941-50-0 D-arabinose diethyl dithioacetal 

Downstream Products

• 106929-09-3 (2S,3R,4R)-2,3-dibenzyloxy-4,5-isopropylidenedioxypentanal 
• 222723-46-8 2-O-acetyl-3,4-di-O-benzyl-5,6-O-(cyclic sulfate)-1-deoxy-1-dimethylphenylsilyl-D-glucitol 
• 222723-43-5 2-O-acetyl-3,4-di-O-benzyl-5,6-O-isopropylidene-1-deoxy-1-dimethylphenylsilyl-D-glucitol 
• 222723-45-7 2-O-acetyl-3,4-di-O-benzyl-1-deoxy-1-dimethylphenylsilyl-D-glucitol 
• 222408-64-2 3,4-di-O-benzyl-1-deoxy-1-dimethylphenylsilyl-D-glucitol 
• 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 
• 222723-47-9 2-O-acetyl-3,6-anhydro-4-O-benzyl-1-deoxy-1-dimethylphenylsilyl-D-glucitol 
• 222555-96-6 2,5-anhydro-3,4-di-O-benzyl-D-mannitol 
• 129115-89-5 3,4-dibenzyloxy-2,5-dihydroxymethyltetrahydrofuran 
• 222960-51-2 2,5-anhydro-3,4-di-O-benzyl-L-iditol 
• 222723-70-8 2-O-acetyl-3,6-anhydro-4-O-benzyl-D-glucitol 
• 222723-71-9 3,6-anhydro-4-O-benzyl-D-glucitol 
• 41107-82-8 2,5-anhydro-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.

Postcondensation modifications of Ugi four-component condensation products: 1-Isocyanocyclohexene as a convertible isocyanide. Mechanism of conversion, synthesis of diverse structures, and demonstration of resin capture

The concept of a 'universal isocyanide' that enables postcondensation modification of Ugi four-component condensation products is introduced. This strategy is suited for the synthesis of libraries. By using 1-isocyanocyclohexene as the isocyanide input in the Ugi reaction, the product cyclohexenamides can be converted to a variety of products. From the original α-(acylamino) amides, new carboxylic acids, esters, and thioesters are produced from acid-activated conversion of the cyclohexenamide moiety. It has been determined that the intermediate in conversion of this type is an oxazolinium-5-one (munchnone) that reacts with many nucleophiles to yield the products above. The munchnone can also undergo cycloaddition with acetylenic dipolarophiles to form pyrroles. Through internal nucleophilic attack, Ugi products are shown to convert to a protected monosaccharide derivative and to 1,4-benzodiazepine-2,5-diones. All of the conversions described consist of a single step. Resin capture of Ugi products is demonstrated, in which a solution condensation reaction is followed by trapping of the products onto solid support resin. Both the trapping step and subsequent cleavage of products from the resin occur in very high yield.