91177-70-7

Basic information

• Product Name: (E)-(S)-5-Phenyl-pent-4-ene-2,3-diol
• CAS NO: 91177-70-7
• Molecular Weight: 178.231
• Mol File: 91177-70-7.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: (E)-(S)-5-Phenyl-pent-4-ene-2,3-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-(S)-5-Phenyl-pent-4-ene-2,3-diol(91177-70-7)
• EPA Substance Registry System: (E)-(S)-5-Phenyl-pent-4-ene-2,3-diol(91177-70-7)

Safety Data

• Hazardous Substances Data: 91177-70-7(Hazardous Substances Data)

Upstream product

• 14371-10-9 (E)-3-phenylpropenal 
• 50-99-7 D-glucose 
• 75927-49-0 pinacol vinylboronate 
• 116696-50-5 Acetic acid (E)-(S)-1-methyl-2-oxo-4-phenyl-but-3-enyl ester 
• 113-24-6 sodium pyruvate 
• 95832-93-2 (S)-3-oxo-5-phenylpent-4-en-2-yl acetate 
• 91111-03-4 1-phenyl-4-(tetrahydropyran-2-yloxy)-1-penten-3-one 
• 119420-93-8 Acetic acid (E)-(S)-2-hydroxy-1-methyl-4-phenyl-but-3-enyl ester 
• 3909-96-4 (1E,3E)-1-phenyl-1,3-pentadiene 
• 92215-95-7 3-hydroxy-5-phenyl-4-penten-2-one 

Downstream Products

• 100560-62-1 2-Methyl-3-((E)-styryl)-1,4-dioxa-spiro[4.5]decane 
• 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 
• 73494-49-2 (2R)-5-Phenyl-2-pentanol 
• 2344-71-0 (S)-(+)-5-phenyl-2-pentanol 

Relevant articles and documents

Copper-Catalyzed Tandem Hydrocupration and Diastereo- and Enantioselective Borylalkyl Addition to Aldehydes

We report the copper-catalyzed stereoselective addition of in situ generated chiral boron-α-alkyl intermediates to various aldehydes including α,β-unsaturated aldehydes under mild conditions. This tandem and multicomponent method facilitated the synthesis of enantiomerically enriched 1,2-hydroxyboronates bearing contiguous stereocenters in good yield with high diastereo- and enantioselectivity up to a ratio greater than 98:2. In particular, α,β-unsaturated aldehydes were successfully used as electrophiles in Cu?H catalysis through 1,2-addition without significant reduction. The resulting 1,2-hydroxyboronates were used in various transformations.

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.