94233-71-3

Basic information

• Product Name: (4R,5S)-5-(phenylmethoxy)hex-1-en-4-ol
• Synonyms: (4R,5S)-5-(phenylmethoxy)hex-1-en-4-ol
• CAS NO: 94233-71-3
• Molecular Weight: 206.285
• Mol File: 94233-71-3.mol
• Article Data: 15

Chemical Properties

• CAS DataBase Reference: (4R,5S)-5-(phenylmethoxy)hex-1-en-4-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (4R,5S)-5-(phenylmethoxy)hex-1-en-4-ol(94233-71-3)
• EPA Substance Registry System: (4R,5S)-5-(phenylmethoxy)hex-1-en-4-ol(94233-71-3)

Safety Data

• Hazardous Substances Data: 94233-71-3(Hazardous Substances Data)

Upstream product

• 54783-72-1 ethyl (S)-2-(benzyloxy)propionate 
• 100-39-0 benzyl bromide 
• 2551-83-9 allyltrimethoxysilane 
• 81445-44-5 (S)-2-(benzyloxy)propanal 
• 100-52-7 benzaldehyde 
• 132836-59-0 (1R,5S,3Z)-5-benzyloxy-1-phenylhex-3-en-1-ol 
• 132836-85-2 (1R,5S,3Z)-1-acetoxy-5-benzyloxy-1-phenyl-3-hexene 
• 53346-05-7 (R)-2-benzyloxypropanal 
• 94233-72-4 (4S,5S)-5-(phenylmethoxy)hex-1-en-4-ol 
• 762-72-1 allyl-trimethyl-silane 
• 1730-25-2 allylmagnesium bromide 
• 106-95-6 allyl bromide 
• 85116-38-7 (+)-diisopinocampheylallylborane 
• 72824-04-5 2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 

Downstream Products

• 1318230-58-8 (+)-2-((2S,3R)-2-(benzyloxy)hex-5-en-3-yloxy)acetic acid 
• 1318230-87-3 anti,anti-(+)-(5S,6S)-5-((S)-1-(benzyloxy)ethyl)-6-vinyl-1,4-dioxan-2-one 
• 476212-29-0 {[(1S,2R)-1-methyl-2-(2-propynyloxy)-4-pentenyl]oxymethyl}benzene 
• 476212-27-8 {[(1S,2R)-2-(2-butynyloxy)-1-methyl-4-pentenyl]oxymethyl}benzene 
• 156327-32-1 (2S,3R)-2-benzyloxy-5-hexen-3-yl acetate 

Relevant articles and documents

Preparation of Monosilyl Acetals from Esters via iBu2AlH Reduction and Trapping with N-(Trimethylsilyl)imidazole. Addition of Allyltrimethylsilane To Yield Homoallylic Alcohols or Ethers

Alkyl esters were reduced with iBu2AlH or a 1:1 mixture of iBu2AlH and iBu3Al (iBu2AlH*iBu3Al or iBu5Al2H), followed by trapping of the resulting tetrahedral intermediate with TMS-imidazole to produce monosilyl acetals.Reaction of the mixed acetals with allyltrimethylsilane in the presence of Lewis acids (Hosomi-Sakurai reaction) generated homoallylic alcohols or ethers selectively, depending on the substitution of the monosilyl acetal.TMS methoxy acetals (MeO-CH-OTMS) and TMS ethoxy acetals bearing additional complexing groups such as MeO- or Ph2C=N- provided alcohols with 1.5:1 - 9:1 threoselectivity, while simple TMS ethoxy acetals provided only ethyl ethers as products.The monosilyl acetal configuration was easily epimerized or racemized, and the configuration of the Hosomi-Sakurai product was apparently independent of the initial monosilyl acetal reactant configuration.

Diastereoselective synthesis of trifluoromethylated 1,3-dioxanes by intramolecular oxa-Michael reaction

A highly diastereoselective synthesis of trifluoromethylated 1,3-dioxanes is described. The reaction proceeds by an addition/oxa-Michael sequence and works efficiently under mild reaction conditions, with a good substrate scope and acceptable to good yiel

Synthesis of chiral oxacyclic dienes via ruthenium-catalyzed enyne metathesis: Useful building blocks for chiral tricyclic oxygen derivatives

Various chiral oxacyclic dienes were synthesized via enyne metathesis using Grubbs catalyst (PCy3)2Cl2Ru=CHPh. A series of substrates bearing a 1,2-diol skeleton was prepared from (2S)-(benzyloxy)-propanal. The enyne metathesis proceeds smoothly in CH2Cl2 at 23°C with a low loading of catalyst (2.0mol%) under ethylene gas (1-2.5atm), giving good yields of products without epimerization at any stereogenic carbon. Heating compound 5 comprising a disubstituted alkyne in benzene (80°C) under nitrogen resulted in formation of two diastereomers via epimerization of the primary product. The epimerization occurs at the oxacyclic carbon rather than the benzyl carbon. Diels-Alder reactions of chiral oxacyclic dienes 19 and 22 with maleic anhydride, maleimide and benzoquinone proceeded with high diastereoselectivities, yielding a single cycloadduct efficiently at ambient conditions. The structures of Diels-Alder adducts were determined by 1H NOE NMR spectra. The cycloadducts were formed via the approach of dienophiles to the diene in endo mode and opposite the substituent of the stereogenic center. The cycloadducts 29 and 31 were transformed into enantiopure tricyclic furans 35 and 38 after transformation of the (2S)-(silyloxy)ethyl group into an acetate group.