320400-14-4

Basic information

• Product Name: 5-benzyldimethylsilyl-3-phenyl-1-(2-tetrahydropyranyloxy)-4-pentyne
• Synonyms: 5-benzyldimethylsilyl-3-phenyl-1-(2-tetrahydropyranyloxy)-4-pentyne
• CAS NO: 320400-14-4
• Molecular Weight: 392.613
• Mol File: 320400-14-4.mol

Chemical Properties

• CAS DataBase Reference: 5-benzyldimethylsilyl-3-phenyl-1-(2-tetrahydropyranyloxy)-4-pentyne(CAS DataBase Reference)
• NIST Chemistry Reference: 5-benzyldimethylsilyl-3-phenyl-1-(2-tetrahydropyranyloxy)-4-pentyne(320400-14-4)
• EPA Substance Registry System: 5-benzyldimethylsilyl-3-phenyl-1-(2-tetrahydropyranyloxy)-4-pentyne(320400-14-4)

Safety Data

• Hazardous Substances Data: 320400-14-4(Hazardous Substances Data)

Upstream product

• 320399-95-9 3-phenyl-1-(2-tetrahydropyranyloxy)-4-pentyne 
• 1833-31-4 benzyl(chloro)dimethylsilane 
• 6921-34-2 benzylmagnesium chloride 
• 220801-86-5 3-phenyl-4-pentyn-1-ol 
• 110-87-2 3,4-dihydro-2H-pyran 

Downstream Products

• 320399-75-5 (Z)-5-benzyldimethylsilyl-3-phenyl-4-penten-1-ol 
• 259874-79-8 N-((Z)-5-benzyldimethylsilyl-3-phenyl-4-pentenyl)-p-toluenesulfonamide 
• 259874-80-1 2-[(Z)-5-(Benzyl-dimethyl-silanyl)-3-phenyl-pent-4-enyl]-isoindole-1,3-dione 
• 80816-30-4 3-phenyl-4-pentenol 
• 460752-83-4 (Z)-5-benzyldimethylsilyl-3-phenyl-4-nonen-1-ol 
• 460752-49-2 (E)-5-benzyldimethylsilyl-5-bromo-3-phenyl-1-(2-tetrahydropyranyloxy)-4-pentene 

Relevant articles and documents

1,2-Silyl-migrative cyclization of vinylsilanes bearing a hydroxy group: Stereoselective synthesis of multisubstituted tetrahydropyrans and tetrahydrofurans

Acid-catalyzed intramolecular addition of a hydroxy group to α-alkylated vinylsilanes has been studied. Treatment of (Z)-5-alkyl-5-silyl-4-penten-1-ols 1 (R = alkyl) with 5 mol % TiCl4 in CHCl3 gave trans-2-alkyl-3-silyltetrahydropyrans 2 exclusively (trans/cis = > 99/1 to 97/3). The cyclization efficiency and rate strongly depended on the geometry of the C-C double bond and the silyl group. The use of (E)-vinylsilanes resulted in lower yields with poor cis-selectivity. In the cyclization of (Z)-1 (R = Bu), the silyl group used, the reaction time, and the yield of 2 were as follows: SiMe2Ph, 9.5 h, 75%; SiMe3, 7.5 h, 66%; SiMePh2, 24 h, 58%; SiMe2-t-Bu, 0.75 h, 85%; SiMe2Bn, 1.5 h, 78%. This 1,2-silyl-migrative cyclization could be applied to stereoselective synthesis of trisubstituted tetrahydropyrans. The acid-catalyzed reaction of 1-, 2-, or 3-substituted (Z)-5-silyl-4-nonen-1-ols 8 gave r-2,t-3,c-6-, r-2,t-3,t-5-, or r-2,t-3,c-4-trisubstituted tetrahydropyrans with high diastereo-selectivity, respectively. (Z)-4-Alkyl-4-silyl-3-buten-1-ols 5 as well as 1 underwent the 1,2-silylmigrative cyclization to give 2-alkyl-3-silyltetrahydrofurans 6 with high trans-selectivity. This silicon-directed cyclization was also available for the stereoselective synthesis of tri- and tetrasubstituted tetrahydrofurans.

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