259874-46-9

Upstream product

• 6921-34-2 benzylmagnesium chloride 
• 1833-31-4 benzyl(chloro)dimethylsilane 
• 5390-04-5 pent-1-yn-5-ol 
• 62992-46-5 1-(tetrahydropyranyloxy)-4-pentyn 
• 97-99-4 Tetrahydrofurfuryl alcohol 
• 259874-44-7 5-(benzyldimethylsilyl)-1-(tetrahydropyran-2′-yloxy)pent-4-yne 

Downstream Products

• 259874-58-3 N-((Z)-5-benzyldimethylsilyl-1-phenyl-4-pentenyl)-p-toluenesulfonamide 
• 259874-52-7 N-((Z)-5-benzyldimethylsilyl-4-pentenyl)-p-toluenesulfonamide 
• 259874-81-2 2-(benzyldimethylsilyl)methyl-1-p-toluenesulfonylpyrrolidine 
• 259874-67-4 N-((Z)-5-benzyldimethylsilyl-4-pentenyl)trifluoromethanesulfonamide 
• 259874-64-1 N-((Z)-5-benzyldimethylsilyl-4-pentenyl)trifluoroacetamide 
• 259874-69-6 t-butoxy N-((Z)-5-benzyldimethylsilyl-4-pentenyl)carbamate 
• 259874-85-6 2-[(benzyl-dimethyl-silanyl)-methyl]-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 259874-65-2 N-((Z)-5-benzyldimethylsilyl-4-pentenyl)methanesulfonamide 
• 259874-62-9 N-((Z)-5-benzyldimethylsilyl-4-pentenyl)acetamide 
• 91645-35-1 (RS)-[1-(toluene-4-sulfonyl)-pyrrolidine-2-yl]-methanol 
• 81097-24-7 N-tosyl-(4-pentenyl)amine 
• 259874-56-1 N-((Z)-5-benzyldimethylsilyl-1-phenyl-4-pentenyl)phthalimide 
• 259874-50-5 (Z)-5-benzyldimethylsilyl-4-penten-1-amine 
• 259874-49-2 (4Z)-5-benzyldimethylsilyl-4-pentenal oxime 

Relevant academic research and scientific papers

Acid-catalyzed cyclization of vinylsilanes bearing a hydroxy group: A new method for stereoselective synthesis of disubstituted tetrahydrofurans

In the presence of a catalytic amount of TsOH or TiCl4, (Z)-5-silyl-4-penten-1-ols ((Z)-1) are smoothly cyclized to 2-silylmethyl-substituted tetrahydrofurans. This cyclization is applicable to the construction of a tetrahydropyran ring. The silyl group and the geometry of the C-C double bond strongly influence the cychzation rate. TBDMS and benzyldimethylsilyl groups considerably accelerate the cyclization in comparison with a dimethylphenylsilyl group, and (E)-vinylsilanes show much lower reactivity than the corresponding (Z)-isomers. The cyclization proceeds by stereospecific syn addition of the hydroxy group. Vinylsilanes 17, 19, and 21, (Z)-5-silyl-4-penten-1-ols bearing a substituent on the methylene tether, smoothly undergo the acid-catalyzed cyclization to give trans-2,5-, cis-2,4-, and trans-2,3-disubstituted tetrahydrofurans, respectively, with moderate to high stereoselectivity. The silyl group of some cychzed products can be easily converted into a hydroxy group with stereochemical retention.

Acid-catalyzed cyclization of vinylsilanes bearing an amino group. Stereoselective synthesis of pyrrolidines

(FORMULA PRESENTED) In the presence of an acid catalyst, vinylsilanes 1 bearing an amino group protected by an electron-withdrawing group were smoothly cyclized to 2-(silylmethyl)pyrrolidines 2. This cyclization was utilized for the stereoselective synthe