105857-60-1

Basic information

• Product Name: Benzeneethanol, b-[(phenylthio)methyl]-, (R)-
• CAS NO: 105857-60-1
• Molecular Formula: C15H16OS
• Molecular Weight: 244.357
• Mol File: 105857-60-1.mol

Chemical Properties

• CAS DataBase Reference: Benzeneethanol, b-[(phenylthio)methyl]-, (R)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzeneethanol, b-[(phenylthio)methyl]-, (R)-(105857-60-1)
• EPA Substance Registry System: Benzeneethanol, b-[(phenylthio)methyl]-, (R)-(105857-60-1)

Safety Data

• Hazardous Substances Data: 105857-60-1(Hazardous Substances Data)

Upstream product

• 105857-46-3 (7S,10R)-7-Isopropyl-10-methyl-3-phenyl-1,5-dioxa-spiro[5.5]undecane 
• 930-69-8 sodium thiophenolate 
• 10317-13-2 3-phenyloxetane 
• 1570-95-2 2-phenylpropane-1, 3-diol 
• 105857-61-2 Methanesulfonic acid (R)-3-[(1R,2S,5R)-2-isopropyl-5-methyl-1-(2-oxo-2-phenyl-ethyl)-cyclohexyloxy]-2-phenyl-propyl ester 
• 105857-59-8 2-[(1R,2S,5R)-2-Isopropyl-5-methyl-1-((R)-2-phenyl-3-phenylsulfanyl-propoxy)-cyclohexyl]-1-phenyl-ethanone 
• 105857-52-1 2-[(1R,2S,5R)-1-((S)-3-Hydroxy-2-phenyl-propoxy)-2-isopropyl-5-methyl-cyclohexyl]-1-phenyl-ethanone 

Downstream Products

• 1123-85-9 (+)-(R)-2-phenylpropanol 

Relevant articles and documents

Highly Enantioselective, Hydrogen-Bond-Donor Catalyzed Additions to Oxetanes

A precisely designed chiral squaramide derivative is shown to promote the highly enantioselective addition of trimethylsilyl bromide (TMSBr) to a broad variety of 3-substituted and 3,3-disubstituted oxetanes. The reaction provides direct and general access to synthetically valuable 1,3-bromohydrin building blocks from easily accessed achiral precursors. The products are readily elaborated both by nucleophilic substitution and through transition-metal-catalyzed cross-coupling reactions. The enantioselective catalytic oxetane ring opening was employed as part of a three-step, gram-scale synthesis of pretomanid, a recently approved medication for the treatment of multidrug-resistant tuberculosis. Heavy-atom kinetic isotope effect (KIE) studies are consistent with enantiodetermining delivery of bromide from the H-bond-donor (HBD) catalyst to the activated oxetane. While the nucleophilicity of the bromide ion is expected to be attenuated by association to the HBD, overall rate acceleration is achieved by enhancement of Lewis acidity of the TMSBr reagent through anion abstraction.

Enantioselective Functionalization of Prochiral Diols via Chiral Spiroketals: Preparation of Optically Pure 2-Substituted 1,3-Propanediol Derivatives and Asymmetric Synthesis of Chroman Ring and Side Chain of α-Tocopherol

The enantioselective functionalization of a prochiral hydroxyl group in 2-substituted 1,3-propanediols (HOCH2CR1R2CH2OH) is presented.The reaction of the bis(trimethylsilyl) derivative of the diol with l-menthone in the presence of trimethylsilyl trifluoromethanesulfonate selectively gave one of the diastereomers of the spiroketal in which the larger substituent (R1) occupies an equatorial position.The equatorial spiroketal was treated with acetophenone enol trimethylsilyl ether in the presence of titanium tetrachloride to give the ring-cleavage product which was produced by the selective cleavage of the equatorial C-O bond.After a proper functionalization of the hydroxyl group, the chiral auxiliary was removed under basic conditions to give the optically pure (>95percent ee) derivatives 5. The stereoselective preparation of the axial spiroketal (R1 = H, R2 = Me) and its ring-cleavage are also described.The potentiality of the present method is demonstrated in an asymmetric synthesis of (2R,6R)-2,6,10-trimethylundecanol and (S)-6-benzyloxy-3,4-dihydro-2,5,7,8-tetramethyl-2H-benzopyran-2-methanol which are key intermediates in the total synthesis of naturally occuring (2R,4'R,8'R)-α-tocopherol.