81053-29-4

Basic information

• Product Name: (2S,7R)-7-[(1R,3E)-1-Chloro-5-hexyn-3-enyl]-2-[(R)-1-bromopropyl]-1-oxacyclohepta-4-ene
• Synonyms: (2S,7R)-7-[(1R,3E)-1-Chloro-5-hexyn-3-enyl]-2-[(R)-1-bromopropyl]-1-oxacyclohepta-4-ene;Isolaurepinnacin
• CAS NO: 81053-29-4
• Molecular Formula: C15H20BrClO
• Molecular Weight: 331.6757
• Mol File: 81053-29-4.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (2S,7R)-7-[(1R,3E)-1-Chloro-5-hexyn-3-enyl]-2-[(R)-1-bromopropyl]-1-oxacyclohepta-4-ene(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,7R)-7-[(1R,3E)-1-Chloro-5-hexyn-3-enyl]-2-[(R)-1-bromopropyl]-1-oxacyclohepta-4-ene(81053-29-4)
• EPA Substance Registry System: (2S,7R)-7-[(1R,3E)-1-Chloro-5-hexyn-3-enyl]-2-[(R)-1-bromopropyl]-1-oxacyclohepta-4-ene(81053-29-4)

Safety Data

• Hazardous Substances Data: 81053-29-4(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 
• 151074-04-3 (5-bromo-4-chloro-5-methoxy-pentyloxy)-triisopropyl-silane 
• 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 
• 187743-89-1 (3S,4S)-3-bromo-4-[(2R)-2-chloro-1-methoxy-5-(triisopropylsiloxy)pentoxy]-7-(trimethylsilyl)-7-octene 
• 1026334-14-4 {(R)-4-[(2R,7S)-7-((S)-1-Bromo-propyl)-2,3,6,7-tetrahydro-oxepin-2-yl]-4-chloro-butoxy}-triisopropyl-silane 
• 151073-98-2 (2S,3S)-3-bromo-1,2-pentanediol, 1-phenylsulfonate ester 
• 187743-78-8 1,1-dimethoxy-5-(triisopropylsiloxy)pent-3-yn-2-one 
• 326853-64-9 (R)-4-[(2R,7S)-7-((S)-1-Bromo-propyl)-2,3,6,7-tetrahydro-oxepin-2-yl]-4-chloro-butyraldehyde 
• 151074-07-6 (2S,7R)-2-[(1S)-1-bromopropyl]-7-[(1R)-chloro-4-hydroxybutyl]-2,3,6,7-tetrahydrooxepin 
• 151074-02-1 (2S)-1,1-dimethoxy-5-(triisopropylsiloxy)pentan-2-ol 
• 151074-03-2 (2R)-2-chloro-1,1-dimethoxy-5-(triisopropylsiloxy)pentane 
• 187743-88-0 ((R)-5-Bromo-4-chloro-5-methoxy-pentyloxy)-triisopropyl-silane 

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.