88157-27-1

Basic information

• Product Name: Phosphonium, [3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]propyl]triphenyl-, iodide
• CAS NO: 88157-27-1
• Molecular Formula: C27H36OPSi.I
• Molecular Weight: 562.546
• Mol File: 88157-27-1.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: Phosphonium, [3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]propyl]triphenyl-, iodide(CAS DataBase Reference)
• NIST Chemistry Reference: Phosphonium, [3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]propyl]triphenyl-, iodide(88157-27-1)
• EPA Substance Registry System: Phosphonium, [3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]propyl]triphenyl-, iodide(88157-27-1)

Safety Data

• Hazardous Substances Data: 88157-27-1(Hazardous Substances Data)

Upstream product

• 18162-48-6 tert-butyldimethylsilyl chloride 
• 73842-99-6 3-tert-butyldimethylsilyloxy-1-propanol 
• 89031-82-3 1-(t-Butyldimethylsilyloxy)-3-chloro-propane 
• 78878-05-4 1-iodo-3-(tert-butyldimethylsilyloxy)propane 
• 603-35-0 triphenylphosphine 
• 627-30-5 1-chloro-3-hydroxypropane 

Downstream Products

• 1000992-99-3 C₁₉H₃₂O₃Si 
• 161984-57-2 (2S,3R,4aS,6R,7S,8aR)-3-Benzyloxy-2-(2-benzyloxy-ethyl)-7-(tert-butyl-dimethyl-silanyloxy)-6-[4-(tert-butyl-dimethyl-silanyloxy)-butyl]-2,4a,6-trimethyl-octahydro-pyrano[3,2-b]pyran 
• 714966-82-2 (E)-3-{2-[(Z)-6-(tert-Butyl-dimethyl-silanyloxy)-hex-3-enyl]-4-methoxy-phenyl}-prop-2-en-1-ol 
• 714966-74-2 (E)-3-{2-[(Z)-6-(tert-Butyl-dimethyl-silanyloxy)-hex-3-enyl]-4-methoxy-phenyl}-acrylic acid ethyl ester 
• 131318-58-6 [3-(tert-butyl-dimethyl-silanyloxy)-propylidene]-triphenyl-λ⁵-phosphane 
• 161984-56-1 (2S,3R,4aS,6R,7S,8aR)-3-Benzyloxy-2-(2-benzyloxy-ethyl)-7-(tert-butyl-dimethyl-silanyloxy)-6-[(Z)-4-(tert-butyl-dimethyl-silanyloxy)-but-1-enyl]-2,4a,6-trimethyl-octahydro-pyrano[3,2-b]pyran 

Relevant articles and documents

Use of the 2-Pyridinesulfonyloxy Leaving Group for the Fast Copper-Catalyzed Coupling Reaction at Secondary Alkyl Carbons with Grignard Reagents

Investigation of the copper-catalyzed coupling reaction of 2-pyridinesulfonates with Grignard reagents revealed that reactions with catalytic Cu(OTf)2 were completed in 40 min. The results differed from those of the previous CuI-catalyzed reactions of tosylates in the presence of additives (LiOMe and TMEDA) for 12-24 h. It was shown that the preferred coordination of the leaving group to the reagents accelerated the reaction. Successful reagents were MeMgCl and other RMgX. Complete inversion was established.

Asymmetric total synthesis of caribenol A via an intramolecular diels-alder reaction

A total synthesis of the caribenol A (1), a novel natural product with an intriguing tetracyclic framework, has been achieved. The synthesis features an intramolecular Diels-Alder (IMDA) reaction for the facile construction of the tricyclic [5-7-6] skelet

Samarium(II) iodide-mediated reductive annulations of ketones bearing a distal vinyl epoxide moiety

Samarium(II) iodide in the presence of hexamethylphosphoramide (HMPA) efficiently promotes the intramolecular coupling of ketones with distal epoxy olefins. The reaction appears to proceed by a mechanism wherein a ketyl couples with the unsaturated epoxide. Subsequent fragmentation of the epoxide ring in compounds 1a-k yields carbocycles 2a-k with an allyl alcohol side chain in good yields, and often with high diastereoselectivity. When tetramethylguanidine was used as an additive instead of HMPA, the desired carbocycle was obtained in good yield, but the diastereoselectivity was diminished. A palladium(0)-catalyzed SmI2 reaction provided the expected product in modest yield, but the sense of diastereoselectivity was reversed. In the latter case, a different reaction mechanism may be involved. Thus, formation of an allylsamarium species may be invoked, with nucleophilic carbonyl addition leading to the observed facial selectivity.