187743-99-3

Basic information

• Product Name: Benzoic acid (S)-1-dimethoxymethyl-4-triisopropylsilanyloxy-but-2-ynyl ester
• Synonyms: Benzoic acid (S)-1-dimethoxymethyl-4-triisopropylsilanyloxy-but-2-ynyl ester
• CAS NO: 187743-99-3
• Molecular Weight: 420.621
• Mol File: 187743-99-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: Benzoic acid (S)-1-dimethoxymethyl-4-triisopropylsilanyloxy-but-2-ynyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Benzoic acid (S)-1-dimethoxymethyl-4-triisopropylsilanyloxy-but-2-ynyl ester(187743-99-3)
• EPA Substance Registry System: Benzoic acid (S)-1-dimethoxymethyl-4-triisopropylsilanyloxy-but-2-ynyl ester(187743-99-3)

Safety Data

• Hazardous Substances Data: 187743-99-3(Hazardous Substances Data)

Upstream product

• 65-85-0 benzoic acid 
• 151074-01-0 (+/-)-1,1-dimethoxy-5-(triisopropylsiloxy)pent-3-yn-2-ol 

Downstream Products

• 187743-83-5 ((S)-4-Benzyloxy-5,5-dimethoxy-pentyloxy)-triisopropyl-silane 
• 187743-84-6 ((S)-4-Benzyloxy-5-methoxy-pentyloxy)-triisopropyl-silane 
• 187744-09-8 (S)-2-Benzyloxy-5-triisopropylsilanyloxy-pentan-1-ol 
• 187744-07-6 (S)-2-Benzyloxy-5-triisopropylsilanyloxy-pentanal 
• 81053-29-4 (+)-isolaurepinnacin 

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.