460752-64-1

Basic information

• Product Name: 5-(benzyldimethylsilyl)pent-4-yn-1-ol
• Synonyms: 5-(benzyldimethylsilyl)pent-4-yn-1-ol
• CAS NO: 460752-64-1
• Molecular Weight: 232.398
• Mol File: 460752-64-1.mol

Chemical Properties

• CAS DataBase Reference: 5-(benzyldimethylsilyl)pent-4-yn-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(benzyldimethylsilyl)pent-4-yn-1-ol(460752-64-1)
• EPA Substance Registry System: 5-(benzyldimethylsilyl)pent-4-yn-1-ol(460752-64-1)

Safety Data

• Hazardous Substances Data: 460752-64-1(Hazardous Substances Data)

Upstream product

• 5390-04-5 pent-1-yn-5-ol 
• 62992-46-5 1-(tetrahydropyranyloxy)-4-pentyn 
• 259874-44-7 5-(benzyldimethylsilyl)-1-(tetrahydropyran-2′-yloxy)pent-4-yne 

Downstream Products

• 1310330-14-3 C₂₆H₄₀O₂Si 
• 1310330-11-0 C₂₃H₃₄O₂Si 
• 1310330-07-4 C₂₂H₃₂O₂Si 
• 1310330-47-2 C₂₈H₄₄O₂Si 
• 1310330-46-1 C₂₄H₃₆O₂Si 
• 1310330-45-0 C₂₅H₃₈O₂Si 
• 1310330-37-0 C₁₆H₂₄OSi 
• 273218-57-8 (E)-5-benzyldimethylsilyl-4-nonen-1-ol 
• 460752-63-0 (Z)-5-benzyldimethylsilyl-5-iodo-1-(2-tetrahydropyranyloxy)-4-pentene 

Relevant articles and documents

Structural diversification of the aminobicyclo[4.3.0]nonane skeleton using alkynylsilyl-derived allylic trichloroacetimidates

The amino substituted bicyclo[4.3.0]nonane is a molecular scaffold found in a wide range of natural products and medicinal agents. Despite this, synthetic methods for the general preparation of this structural motif are sparse. Here we evaluate a diastere

Stereoselective synthesis of E,Z-configured 1,3-dienes by ring-closing metathesis. Application to the total synthesis of lactimidomycin

Strategic positioning of a silyl group on the diene unit of a diene-ene substrate allows rigorous regio- and stereocontrol to be exerted during metathesis-based macrocyclization reactions. The versatility of this concise approach to E,Z-configured 1,3-die

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.