67470-74-0

Upstream product

• 119420-93-8 Acetic acid (E)-(S)-2-hydroxy-1-methyl-4-phenyl-but-3-enyl ester 
• 14371-10-9 (E)-3-phenylpropenal 
• 50-99-7 D-glucose 
• 92215-95-7 3-hydroxy-5-phenyl-4-penten-2-one 
• 91111-03-4 1-phenyl-4-(tetrahydropyran-2-yloxy)-1-penten-3-one 
• 75-07-0 acetaldehyde 
• 113-24-6 sodium pyruvate 
• 116696-50-5 Acetic acid (E)-(S)-1-methyl-2-oxo-4-phenyl-but-3-enyl ester 
• 910792-92-6 (3S,4S,Z)-4-(tert-butyldimethylsiloxy)-1-phenyl-3-(triisopropylsiloxy)-2-(trimethylsilyl)pent-1-ene 
• 95832-93-2 (S)-3-oxo-5-phenylpent-4-en-2-yl acetate 

Downstream Products

• 73494-49-2 (2R)-5-Phenyl-2-pentanol 
• 2344-71-0 (S)-(+)-5-phenyl-2-pentanol 
• 116696-54-9 (3R,4S,1E)-3,4-(cyclohexylidenedioxy)-1-phenyl-1-pentene 
• 116696-53-8 (3S,4S,1E)-3,4-(cyclohexylidenedioxy)-1-phenyl-1-pentene 
• 100560-62-1 2-Methyl-3-((E)-styryl)-1,4-dioxa-spiro[4.5]decane 
• 73444-39-0 (2R,3S)-5-Phenylpentane-2,3-diol 
• 86088-37-1 (2R,3R)-2-Methyl-3-phenethyl-oxirane 
• 73444-38-9 (2S,3R)-2,3-Ditosyloxy-5-phenylpentane 
• 73444-37-8 (2S,3R)-5-Phenyl-3-tosyloxy-2-pentanol 
• 73444-36-7 (2S,3R)-5-Phenyl-2-tosyloxy-3-pentanol 
• 71747-37-0 (S)-1-phenylpentan-3-ol 
• 82043-31-0 (2S,3R) 2,3-isopropylidenedioxy-5-phenylpent-4-ene 
• 73444-35-6 (2S,3R)-5-Phenylpentane-2,3-diol 

Relevant academic research and scientific papers

Highly diastereoselective preparation of anti-1,2-diols by catalytic addition of alkynylsilanes to α-silyloxyaldehydes

The catalytic, diastereoselective coupling of α-silyloxy aldehydes and alkynylsilanes catalyzed by a nickel(0) N-heterocyclic carbene complex provides an effective entry to anti-1,2-diols. The scope of couplings and extent of diastereoselection are excell

Extractive biocatalysis: A powerful tool in selectivity control in yeast biotransformations

The effect of absorbing resins on the yeast reduction of α,β- unsaturated carbonyl compounds is reported. Enantioselectivity, chemoselectivity and space-time yields of the biotransformation are impressively enhanced. The distribution of substrates and products between the resin and the water phase shows that the improved selectivity has to be attributed to the control of substrate concentration.

Improved Conditions for the production and Chatacterization of 1-Arylpropane-1,2-diols and Related Compounds

Improved conditions for the production and characterization of 1-arylpropane-1,2-diols and related compounds were developed.Experimental conditions providing highly enhanced activity of pyruvate decarboxylase in bakers' yeast in the presence of pyruvate, thiamine pyrophosphate, and magnesium(II) salt were applied to the preparation of (R)-1-hydroxy-1-phenyl-2-propanone from benzaldehyde.Subsequent reduction with bakers' yeast efficiently afforded 1-phenyl-1,2-propanediol (35percent).The composition of its stereoisomers was precisely determined, and the major (1R,2S)-isomer (89percent of the total mixture) could be isolated by recrystallizing the corresponding benzoate.The analytical method for identifying the stereoisomeric composition was also effective for the determination of 5-phenyl-4-pentene-2,3-diol, the biotransformation product from cinnamaldehyde, the vinylogous substrate of benzaldehyde.Furthermore, the structural characterization of 1(2-furyl)propane-1,2-diol, which was obtained from furfural (28percent) by the action of brewers' yeast Saccharomyces cerevisiae (carlsbergensis), is described.The major (1S,2S)-isomer could be isolated by recrystallizing the crude product.

Decarboxylative Incorporation of α-Oxobutyrate and α-Oxovalerate into (R)-α-Hydroxyethyl- and n-Propyl Ketones on Reaction with Aromatic and α,β-Unsaturated Aldehydes in Baker's Yeast

Decarboxylative incorporation of linear C3, C4, and C5 α-oxo acids into (R) α-hydroxy ketones (2), (9) and (10) is observed when benzaldehyde (1) is incubated with baker's yeast; α,β-unsaturated aldehydes (11) and (15) with the C3 and C4 acids yield (R)-α

Fluoride Ion Catalyzed Reduction of Aldehydes and Ketones with Hydrosilanes. Synthetic and Mechanistic Aspects and an Application to the Threo-Directed Reduction of α-Substituted Alkanones

Reduction of aldehydes and ketones with hydrosilanes proceeded in the presence of a catalytic amount of tetrabutylammonium fluoride or tris(diethylamino)sulfonium difluorotrimethylsilicate in aprotic polar solvents under mild conditions.A significant isotope effect (kH/kD = 1.50) was observed in competitive reduction of acetophenone with HSiMe2Ph and DSiMe2Ph.The reaction was of first order in the concentration of an aprotic polar solvent HMPA.Reduction of 2-methylcyclohexanone gave cis-2-methylcyclohexanol with selectivities up to 95percent.The kinetic and stereochemical results suggest that a hexavalent fluorosilicate - is involved. α-Alkoxy (acyloxy or dimethylamino) ketones were transformed to threo alcohols in high diastereoselectivities.The reduction was also applied to α-methyl-β-keto amides, RCOCH(MeCONR)2, to afford the corresponding threo alcohols in >98percent selectivity.The threo selectivity is explained in terms of the Felkin-Anh model in which interaction of carbonyl oxygen with a countercation is ideally suppressed.The threo-directed reduction was applied to (R)-1-phenyl-4-(2-tetrahydropyranyloxy)-1-penten-3-one and N-(2-benzoylpropanoyl)piperidine.The resulting threo alcohols were respectively converted into (2R,3S)-2,3-(cyclohexylidenedioxy)butanal, a key intermediate of daunosamine synthesis, and into a pharmacologically useful compound threo-N-(3-hydroxy-2-methyl-3-phenylpropyl)piperidine.

SYNTHESIS OF 1-SUBSTITUTED (S)-4-ACETOXY-1-PENTEN-3-ONES USING (S)-LACTIC ACID AS A CHIRAL SOURCE AND THEIR SYNTHETIC REACTIONS

Ylide reaction of (S)-3-acetoxy-1-triphenylphosphoranylidene-2-butanone, derived from (S)-lactic acid, with aldehydes gives 1-substituted (S)-4-acetoxy-1-penten-3-one derivatives, which are shown to be transformed into useful chiral compouds by stereosele

On the Steric Course of Bakers's Yeast Reduction of α-Hydroxy Ketones

The baker's yeast mediated conversion of the α-hydroxy ketones 1-6 into the diols 8-14 is reported.

Synthesis of N-Trifluoroacetyl-L-acosamine and -L-daunosamine

N-Trifluoroacetyl-L-acosamine (18) has been chirally synthesised from the chiral educt (1) obtained from cinnamaldehyde and bakers' yeast, whereas N-trifluoroacetyl-L-daunosamine (17) was obtained by inverting the configuration at C-4 of the intermediate