67470-70-6

Basic information

• Product Name: (2S,3R)-2,3-Dihydroxy-4-methyl-5-phenylpent-4-ene
• Synonyms: (2S,3R)-2,3-Dihydroxy-4-methyl-5-phenylpent-4-ene
• CAS NO: 67470-70-6
• Molecular Weight: 192.258
• Mol File: 67470-70-6.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (2S,3R)-2,3-Dihydroxy-4-methyl-5-phenylpent-4-ene(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3R)-2,3-Dihydroxy-4-methyl-5-phenylpent-4-ene(67470-70-6)
• EPA Substance Registry System: (2S,3R)-2,3-Dihydroxy-4-methyl-5-phenylpent-4-ene(67470-70-6)

Safety Data

• Hazardous Substances Data: 67470-70-6(Hazardous Substances Data)

Upstream product

• 101-39-3 2-methyl-3-phenyl-2-propenal 
• 50-99-7 D-glucose 
• 15174-47-7 α-methyl-trans-cinnamaldehyde 
• 92215-96-8 (E)-3-Hydroxy-4-methyl-5-phenyl-pent-4-en-2-one 
• 92010-47-4 (E)-4-Hydroxy-2-methyl-1-phenyl-pent-1-en-3-one 

Downstream Products

• 100-52-7 benzaldehyde 
• 74966-76-0 N-((2S,3R,4S,6R)-3-Hydroxy-6-methoxy-2,4-dimethyl-tetrahydro-pyran-4-yl)-benzamide 
• 89822-02-6 N-((2S,3S,4R,6S)-3,6-Dihydroxy-2,4-dimethyl-tetrahydro-pyran-4-yl)-benzamide 
• 81653-07-8 N-((2S,3S,4R,6R)-3,6-Dihydroxy-2,4-dimethyl-tetrahydro-pyran-4-yl)-benzamide 
• 81653-06-7 N-((2S,3R,4S,6R)-3,6-Dihydroxy-2,4-dimethyl-tetrahydro-pyran-4-yl)-benzamide 
• 89822-01-5 N-((2S,3S,4S,6S)-3,6-Dihydroxy-2,4-dimethyl-tetrahydro-pyran-4-yl)-benzamide 
• 81653-08-9 N-benzoyl-L-vancosamine 
• 81703-35-7 N-[(R)-1-((1S,2S)-1,2-Dihydroxy-propyl)-1-methyl-but-3-enyl]-benzamide 
• 81653-03-4 N-[(S)-1-((1R,2S)-1,2-Dihydroxy-propyl)-1-methyl-but-3-enyl]-benzamide 
• 81653-09-0 (3aR,4S,7aR)-6-Ethoxy-4,7a-dimethyl-2-phenyl-3a,6,7,7a-tetrahydro-4H-pyrano[4,3-d]oxazole 
• 81653-02-3 C₁₄H₁₉NO₂S 
• 87841-67-6 C₂₀H₂₄O 
• 87841-67-6 C₂₀H₂₄O 
• 87841-64-3 C₂₀H₂₄O 

Relevant articles and documents

Stereochemical course of baker's yeast mediated reduction of the tri- and tetrasubstituted double bonds of substituted cinnamaldehydes

A comprehensive study of the stereochemical course of baker's yeast mediated reduction of substituted cinnamaldehydes is reported. Hydride addition to the β position of β-methylcinnamaldehydes preferentially afforded isomers of (3S)-3-phenylbutan-1-ol. The reduction of (E)-2,3-dimethyl- cinnamaldehyde (15) produced a mixture of (2S,3S)- and (2R,3S)-2-methyl-3- phenylbutan-1-ol (13 and 14), respectively, with 93 % ee. Conversely (Z)-2,3-dimethylcinnamal-dehyde (16) afforded, a mixture of 13 and 14 with 33 % ee. Accordingly, the reduction of trisubstituted β-methylcinnam-aldehydes 34 and 35 proceeded with the same stereochemical preference and with higher enantioselectivity to give (S) 3-phenylbutan-1-ol (37). In addition, deuterium, incorporation and 2H NMR studies demonstrated that the addition of the second hydrogen atom to the a position proceeded with very low stereochemical control and the overall process is formally a mixture of cis/trans hydrogen addition to the double bond. Alternatively, α-methylcinnamaldehyde is reduced to (S)-2-methyl-3-phenylpropan-1-ol (24) with preferential addition of the hydride to the opposite β face with good stereochemical control of the irons addition of hydrogen to the double bond. Wiley-VCH Verlag GmbH & Co. KGaA.

Synthesis of (-)-Frontalin from the (2S,3R)-Diol prepared from α-Methylcinnamaldehyde and Fermenting Baker's Yeast

The synthesis of (-)-frontalin (13) from the (2S,3R)-diol (2b), through the intermediacy of the C5 (3S,4S) methyl ketone (6) and of the C11 adduct (8), is reported.