67180-09-0

Basic information

• Product Name: (2R,3S)-erythro-3-Methyl-4-phenyl-2-butanol
• Synonyms: (2R,3S)-erythro-3-Methyl-4-phenyl-2-butanol
• CAS NO: 67180-09-0
• Molecular Weight: 164.247
• Mol File: 67180-09-0.mol

Chemical Properties

• CAS DataBase Reference: (2R,3S)-erythro-3-Methyl-4-phenyl-2-butanol(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3S)-erythro-3-Methyl-4-phenyl-2-butanol(67180-09-0)
• EPA Substance Registry System: (2R,3S)-erythro-3-Methyl-4-phenyl-2-butanol(67180-09-0)

Safety Data

• Hazardous Substances Data: 67180-09-0(Hazardous Substances Data)

Upstream product

• 917-64-6 methyl magnesium iodide 
• 5445-77-2 2-benzylpropionaldehyde 
• 90106-96-0 Bromomethyl-dimethyl-((E)-1-methyl-3-phenyl-allyloxy)-silane 
• 104174-46-1 C₁₁H₁₄O 
• 25181-26-4 (1α,2β,3β)-1,2-dimethyl-3-phenylcyclopropane 
• 7653-96-5 r-1-phenyl-cis-2,cis-3-dimethylcyclopropane 
• 925669-95-0 2,3-cis-epoxybutane 
• 6921-34-2 benzylmagnesium chloride 
• 196106-01-1 (R)-3-methyl-2-phenylbutan-1-amine 
• 67152-34-5 (R)-3-Methyl-2-phenylbutyltosylat 
• 766-04-1 benzyllithium 
• 2550-27-8 (3S)-3-methyl-4-phenylbutan-2-one 
• 42968-14-9 (E)-3-methyl-4-phenyl-3-buten-2-one 
• 100-52-7 benzaldehyde 

Relevant articles and documents

Diastereoselective Copper-Mediated Cross-Couplings between Stereodefined Secondary Alkylcoppers with Bromoalkynes

A copper(I)-mediated cross-coupling of stereodefined secondary alkyllithiums with bromoalkynes provided stereodefined alkynes with high diastereoselectivity (dr up to 98:2). This cross-coupling was extended to various secondary alkyllithiums bearing a remote oxygen functionality, and the alkyne synthesis was also performed with optically enriched alkyl iodides (up to 99% ee) providing, after cross-coupling, alkynes bearing two stereocenters (dr = 93:7; up to 99% ee).

Stereoselective Synthesis and Retentive Trapping of α-Chiral Secondary Alkyllithiums Leading to Stereodefined α,β-Dimethyl Carboxylic Esters

The treatment of α-chiral secondary alkyl iodides with tBuLi at ?100 °C leads to the corresponding secondary alkyllithiums with high retention of configuration. Subsequent quenching with various electrophiles such as Bu2S2, DMF, MeOB(OR)2, or Et2CO provides the desired products with retention of configuration. Furthermore, a transmetalation with CuBr?P(OEt)3also allows retentive trapping with acid chlorides and ethylene oxide. The quenching of the resulting alkyllithiums with ClCO2Et furnishes stereoselectively syn- and anti-ethyl-2,3-dimethyl ester carboxylates (d.r.>94 %). Related esters bearing three adjacent stereo-controlled centers (stereotriads) have also been prepared. This method has been applied to the synthesis of the ant pheromone (±)-lasiol in 26 % overall yield (four steps) with d.r.=97:3 starting from commercially available cis-2,3-epoxybutane.

Multi-enzyme cascade synthesis of the most odorous stereoisomers of the commercial odorant Muguesia

The most odorous stereoisomers of the chiral commercial fragrance Muguesia are prepared by a very effective linear biocatalysed cascade reaction, in which a suitable unsaturated ketone is submitted to the sequential action of two enzymes, an ene-reductase and an alcohol dehydrogenase, which are added together to the same reaction vessel with the cofactor regeneration system. Two stereogenic centres in 1,2 relative position are thus created under high stereochemical control by a two-step one-pot enzymatic procedure.

N-heterocyclic carbene-catalyzed hydrosilylation of styryl and propargylic alcohols with dihydrosilanes

Reducing alkenes to tears: Addition of structurally diverse N-heterocyclic carbenes (NHCs) to silicon allows the reduction of propargylic and styryl alcohols through an organocatalyzed silylation/direct hydride transfer tandem reaction (see scheme). Catalytic turnover is enabled by the switch to and from hypervalent silicon. This provides a new synthetic application of NHC-main group element complexes. Copyright

Chirality and fragrance chemistry: Stereoisomers of the commercial chiral odorants muguesia and pamplefleur

(Chemical Equation Presented) The work describes the enzyme-mediated preparation and the odor evaluation of the single stereoisomers of the commercial odorants Muguesia and Pamplefleur. The synthetic approach to Muguesia stereoisomers helped to clear the assignment of the relative configuration of intermediate diols 5. The odor response of Pamplefleur isomers was found to be rather unusual. No stereoisomer prevailed, but each one played a definite role in establishing the odor sensation of the final blend.

Diastereoselective addition of organozinc reagents to 2-alkyl-3- (arylsulfanyl)propanals

The preparation of compounds incorporating the 3-hydroxy-2-methyl-1-alkyl moiety of high diastereomeric purity is described. Such compounds can serve as potential building blocks for the preparation of several kinds of natural products. Diastereoselective synthesis of two potential pine sawfly pheromone components, one the pure racemic threo-isomer of 3-methylpentadecan-2-ol and the other the racemic erythro-isomer of 3-methyltridecan-2-ol are described. The diastereoselective addition of R2Zn (R=Me, Et and n-Bu) to several 2-alkyl-3-(arylsulfanyl)propanals in the presence of a Lewis acid and CH 2Cl2 as solvent was studied. An excellent diastereomeric ratio (95/5 anti-Cram/Cram) was obtained with 2-[(phenylsulfanyl)methyl] pentanal, 2-[(phenylsulfanyl)methyl]decanal and 2-[(phenylsulfanyl)methyl] dodecanal and Me2Zn in the presence of TiCl4. (a) Lewis acid catalysed dimethylzinc addition; (b) 1. Prot. and oxidation to sulfone, 2. Alkylation; (c) Deprot. and desulfonation; (d) Desulfurisation.

Three-electron S(N)2 reactions of arylcyclopropane cation radicals. 1. Mechanism

The mechanism of photosensitized nucleophilic substitution reactions on arylcyclopropanes was investigated. Stereochemical experiments with methanol, water, and cyanide as nucleophiles showed that the reactions occurred stereospecifically with complete inversion of configuration at the carbon atom undergoing substitution. Independent generation of the arylcyclopropane cation radicals by nanosecond transient methods showed that they reacted rapidly with nucleophiles with kinetics that were first-order in both the cation radical and the nucleophiles. Through a combination of transient kinetics and steady-state Stern-Volmer quenching experiments, the reaction of the phenylcyclopropane cation radical with methanol was kinetically correlated with the formation of the substitution product. The reaction of phenylcyclopropane cation radical with a series of alcohols as nucleophiles showed small steric effects.

Enantiopreference of Lipase from Pseudomonas cepacia toward Primary Alcohols

We propose an empirical rule that predicts which enantiomer of primary alcohol reacts faster in reactions catalyzed by lipase from Pseudomonas cepacia (PCL).This rule, based on the size of the substituents at the stereocenter, shows an 89percent reliability (correct for 54 of 61 examples).This rule is not reliable for primary alcohols that have an oxygen atom attached to the stereocenter; we excluded these alcohols from the tally above.Surprisingly, the sense of enantiopreference of PCL toward primary alcohols is opposit to its enantiopreference toward secondary alcohols.That is, the OH of secondary alcohols and the CH2OH of primary alcohols point in opposite directions.We suggest, however, that this opposite orientation does not imply a different position of the substituents in the active site of the lipase.Instead, PCL accommodates the extra CH2 in primary alcohols as a kink between the stereocenter and the oxygen which allows a similar position of the alcohols by increasing the diffrence in the size of the substituents but did not find a consistent increase in enantioselectivity.We suggest that high enantioselectivity toward primary alcohols requires not only a significant difference in the size of the substituents, but also control of the conformation along the C(1)-C(2) bond.

Amphiphilic Reactions by Means of Exceptionally Bulky Organoaluminum Reagents. Rational Approach for Obtaining Unusual Equatorial, Anti-Cram, and 1,4 Selectivity in Carbonyl Alkylation

Exceptionally bulky, oxygenophilic organoaluminum reagents, methylaluminum bis(2,6-di-tert-4-alkylphenoxide) (MAD and MAT), have been successfully utilized for stereoselective activation of carbonyl moiety.Combination of MAD or MAT with carbon nucleophiles such as organolithiums or Grignard reagents generates a new amphiphilic reaction system in which the alkylation may be interpreted as the nucleophilic addition of a reactive organometallic compound to an electrophilically activated carbonyl substrate in order to account for the regio- and stereochemical consequences.In contrast to the ordinary alkylations, the amphilic alkylation disclosed herein would be categorized into the new, yet unexplored class of alkylation that exhibits high chemoselectivity to carbonyl compounds, and more significantly it allows excellent equatorial and anti-Cram selectivity in carbonyl alkylations, hitherto difficult by the existing methodologies.Further, unusual conjugate addition of organolithium reagents to α,β-unsaturated carbonyl compounds has been accomplished by using the amphiphilic reaction system.