122888-52-2

Upstream product

• 110-87-2 3,4-dihydro-2H-pyran 
• 40365-61-5 2-(but-3-yn-1-yloxy)tetrahydropyran 
• 768-33-2 phenyldimethylsilyl chloride 

Downstream Products

• 104066-54-8 dimethyl(phenyl)(4-((tetrahydro-2H-pyran-2-yl)oxy)but-1-en-2-yl)silane 
• 122888-45-3 dimethylphenyl[(Z)-4-(tetrahydropyran-2-yloxy)but-1-enyl]silane 
• 122888-57-7 (Z)-(4S,5RS)-acetyloxy-1-<4-(dimethylphenylsilyl)-3-butenyl>-5-phenylthio-2-pyrrolidinone 
• 122888-59-9 (E)-3S-1-acetyloxy-1-<4-(dimethylphenylsilyl)-3-butenyl>-2,5-pyrrolidinedione 
• 122888-54-4 (Z)-3S-acetyloxy-1-<4-(dimethylphenylsilyl)-3-butenyl>-2,5-pyrrolidinedione 
• 122888-55-5 (Z)-(4S,5RS)-4,5-diacetyloxy-1-<4-(dimethylphenylsilyl)-3-butenyl>-2-pyirrolidinone 
• 460752-70-9 (Z)-7-benzyloxy-4-dimethylphenylsilyl-3-hepten-1-ol 
• 460752-71-0 (E)-4-dimethylphenylsilyl-3-octen-1-ol 
• 198411-07-3 (Z)-4-dimethylphenylsilyl-3-octen-1-ol 
• 460752-61-8 (Z)-4-dimethylphenylsilyl-4-iodo-1-(2-tetrahydropyranyloxy)-3-butene 
• 460752-39-0 (E)-4-bromo-4-dimethylphenylsilyl-1-(2-tetrahydropyranyloxy)-3-butene 
• 122888-53-3 (Z)-4-(dimethyl(phenyl)silyl)but-3-en-1-ol 

Relevant academic research and scientific papers

Configuration-dependent ring opening of silyloxiranes: synthesis of functionalized alkenes or tetrahydrofurans

cis- and trans-Silyloxiranes with a potential tosylate or bromide leaving group in the β position are available by the diastereospecific reduction of the corresponding alkynes with DIBAL-H and hydrosilylation with silanes, respectively. In the reaction wi

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.