(2S,3R)-2,3-Dihydroxy-4-methyl-5-phenylpent-4-ene

Base Information

• Chemical Name: (2S,3R)-2,3-Dihydroxy-4-methyl-5-phenylpent-4-ene
• CAS No.: 67470-70-6
• Molecular Formula: C₁₂H₁₆O₂
• Molecular Weight: 192.258
• Mol file: 67470-70-6.mol

Synonyms:(2S,3R)-2,3-Dihydroxy-4-methyl-5-phenylpent-4-ene

Chemical Property of (2S,3R)-2,3-Dihydroxy-4-methyl-5-phenylpent-4-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R)-2,3-Dihydroxy-4-methyl-5-phenylpent-4-ene

There total 4 articles about (2S,3R)-2,3-Dihydroxy-4-methyl-5-phenylpent-4-ene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 15.0%

2-methyl-3-phenyl-2-propenal (101-39-3) → (S)-2-methyl-3-phenylpropan-1-ol (7384-80-7,77943-96-5,78964-61-1,22436-06-2) + 2-methyl-3-phenylprop-2-en-1-ol (1504-55-8) + (2S,3R)-2,3-Dihydroxy-4-methyl-5-phenylpent-4-ene (67470-70-6)

Guidance literature:

With baker's yeast; D-glucose; In ethanol; water; at 20 ℃; for 96h; optical yield given as %ee; enantioselective reaction;

DOI:10.1002/ejoc.200900827

Reference yield:

D-glucose (50-99-7) + α-methyl-trans-cinnamaldehyde (15174-47-7) → (2S,3R)-2,3-Dihydroxy-4-methyl-5-phenylpent-4-ene (67470-70-6)

Guidance literature:

With disodium hydrogenphosphate; In water; at 30 ℃; for 12h; baker's yeast;

DOI:10.1039/P19830000241

Reference yield:

(E)-4-Hydroxy-2-methyl-1-phenyl-pent-1-en-3-one (92010-47-4) → (2S,3R)-2,3-Dihydroxy-4-methyl-5-phenylpent-4-ene (67470-70-6) + (2R,3R,E)-4-methyl-5-phenylpent-4-ene-2,3-diol (92215-98-0)

Guidance literature:

With baker's yeast; In ethanol; water; for 12h; Yield given. Yields of byproduct given; Ambient temperature;

DOI:10.1021/jo00195a051

upstream raw materials:

(E)-4-Hydroxy-2-methyl-1-phenyl-pent-1-en-3-one

(E)-3-Hydroxy-4-methyl-5-phenyl-pent-4-en-2-one

D-glucose

α-methyl-trans-cinnamaldehyde

Downstream raw materials:

(2S,3R)-2-(Benzoyloxy)-3-hydroxy-4-methyl-5-phenylpent-4-ene

Toluene-4-sulfonic acid (E)-(1S,2R)-2-hydroxy-1,3-dimethyl-4-phenyl-but-3-enyl ester

(4R,5R)-2,2,4-Trimethyl-5-((E)-1-methyl-2-phenyl-vinyl)-[1,3]dioxolane

(3R,4S)-3,4-isopropylidenedioxy-2-methyl-1-phenylpent-1-ene

Refernces

• 1、 Fuganti, Claudio,Grasselli, Piero,Servi, Stefano,Spreafico, Franco,Zirotti, Carlo,Casati, Paolo. "On the Steric Course of Bakers's Yeast Reduction of α-Hydroxy Ketones". . p. 4087 - 4089. Retrieved 2007/10/02.