187743-84-6

Basic information

• Product Name: ((S)-4-Benzyloxy-5-methoxy-pentyloxy)-triisopropyl-silane
• Synonyms: ((S)-4-Benzyloxy-5-methoxy-pentyloxy)-triisopropyl-silane
• CAS NO: 187743-84-6
• Molecular Weight: 380.643
• Mol File: 187743-84-6.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: ((S)-4-Benzyloxy-5-methoxy-pentyloxy)-triisopropyl-silane(CAS DataBase Reference)
• NIST Chemistry Reference: ((S)-4-Benzyloxy-5-methoxy-pentyloxy)-triisopropyl-silane(187743-84-6)
• EPA Substance Registry System: ((S)-4-Benzyloxy-5-methoxy-pentyloxy)-triisopropyl-silane(187743-84-6)

Safety Data

• Hazardous Substances Data: 187743-84-6(Hazardous Substances Data)

Upstream product

• 187743-81-3 ((S)-1-Phenyl-ethyl)-carbamic acid (S)-1-dimethoxymethyl-4-triisopropylsilanyloxy-but-2-ynyl ester 
• 187743-99-3 Benzoic acid (S)-1-dimethoxymethyl-4-triisopropylsilanyloxy-but-2-ynyl ester 
• 187743-83-5 ((S)-4-Benzyloxy-5,5-dimethoxy-pentyloxy)-triisopropyl-silane 
• 187744-07-6 (S)-2-Benzyloxy-5-triisopropylsilanyloxy-pentanal 
• 151074-09-8 (2S)-1,1-dimethoxy-5-(triisopropylsiloxy)pent-3-yn-2-ol 
• 151074-01-0 (+/-)-1,1-dimethoxy-5-(triisopropylsiloxy)pent-3-yn-2-ol 
• 187743-78-8 1,1-dimethoxy-5-(triisopropylsiloxy)pent-3-yn-2-one 
• 151074-02-1 (2S)-1,1-dimethoxy-5-(triisopropylsiloxy)pentan-2-ol 
• 100-39-0 benzyl bromide 
• 187744-09-8 (S)-2-Benzyloxy-5-triisopropylsilanyloxy-pentan-1-ol 
• 74-88-4 methyl iodide 

Relevant articles and documents

Total synthesis of (+)-isolaurepinnacin. Use of acetal-alkene cyclizations to prepare highly functionalized seven-membered cyclic ethers

The first synthesis of the title compound is described. The synthesis features an acetal-vinylsilane cyclization to stereoselectively form the cis-2,7-disubstituted oxepene ring and introduce Δ4 unsaturation. Starting with (2R,3S)-2,3-epoxypentan-1-ol (16), mixed acetal 10 is formed in five steps and 72% overall yield. Treatment of 10 with excess BC13 in CH2Cl2 at -78 → 0°C promotes cyclization to afford Δ4-oxepene 39 in 90% yield after deprotection of the silyl ether. Elaboration of the (E)-enyne functionality of the six-carbon side chain completes the synthesis of (±)-isolaurepinnacin.