(2S,3S,4E)-(-)-3-Hydroxy-2-methyl-5-phenyl-4-pentensaeure-methylester

Base Information

• Chemical Name: (2S,3S,4E)-(-)-3-Hydroxy-2-methyl-5-phenyl-4-pentensaeure-methylester
• CAS No.: 90695-53-7
• Molecular Formula: C₁₃H₁₆O₃
• Molecular Weight: 220.268
• Mol file: 90695-53-7.mol

Synonyms:(2S,3S,4E)-(-)-3-Hydroxy-2-methyl-5-phenyl-4-pentensaeure-methylester

Chemical Property of (2S,3S,4E)-(-)-3-Hydroxy-2-methyl-5-phenyl-4-pentensaeure-methylester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4E)-(-)-3-Hydroxy-2-methyl-5-phenyl-4-pentensaeure-methylester

There total 17 articles about (2S,3S,4E)-(-)-3-Hydroxy-2-methyl-5-phenyl-4-pentensaeure-methylester 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: 72.0%

Methyl 2-methyl-3-oxo-5-phenyl-4-pentenoate (86853-06-7) → (E)-(2S,3S)-3-Hydroxy-2-methyl-5-phenyl-pent-4-enoic acid methyl ester (67498-12-8,67498-20-8,75684-48-9,75684-49-0,79868-64-7,82444-22-2,82444-23-3,86853-07-8,88644-04-6,90695-45-7,90695-53-7,107243-54-9,117858-76-1,117858-77-2,117858-78-3,117858-80-7,117859-44-6) + (E)-syn-methyl 3-hydroxy-2-methyl-5-phenyl-4-pentanoate (67498-12-8,67498-20-8,75684-48-9,75684-49-0,79868-64-7,82444-22-2,82444-23-3,86853-07-8,88644-04-6,90695-45-7,90695-53-7,107243-54-9,117858-76-1,117858-77-2,117858-78-3,117858-80-7,117859-44-6)

Guidance literature:

With zinc(II) tetrahydroborate; In diethyl ether; at 0 ℃;

DOI:10.1016/S0040-4039(00)87009-4

Reference yield: 72.0%

Methyl 2-methyl-3-oxo-5-phenyl-4-pentenoate (86853-06-7) → (E)-(2S,3S)-3-Hydroxy-2-methyl-5-phenyl-pent-4-enoic acid methyl ester (67498-12-8,67498-20-8,75684-48-9,75684-49-0,79868-64-7,82444-22-2,82444-23-3,86853-07-8,88644-04-6,90695-45-7,90695-53-7,107243-54-9,117858-76-1,117858-77-2,117858-78-3,117858-80-7,117859-44-6) + (E)-syn-methyl 3-hydroxy-2-methyl-5-phenyl-4-pentanoate (67498-12-8,67498-20-8,75684-48-9,75684-49-0,79868-64-7,82444-22-2,82444-23-3,86853-07-8,88644-04-6,90695-45-7,90695-53-7,107243-54-9,117858-76-1,117858-77-2,117858-78-3,117858-80-7,117859-44-6)

Guidance literature:

With zinc(II) tetrahydroborate; In diethyl ether; at 0 ℃;

DOI:10.1016/S0040-4039(00)87009-4

Reference yield:

methanol (67-56-1) + C22H23NO4 → (2S,3S,4E)-(-)-3-Hydroxy-2-methyl-5-phenyl-4-pentensaeure-methylester (90695-53-7)

Guidance literature:

With dmap; at 20 ℃; for 12h;

DOI:10.1016/j.tetlet.2016.01.095

upstream raw materials:

diazomethane

(E)-(2S,3S)-3-Hydroxy-2-methyl-5-phenyl-pent-4-enoic acid (1R,2S)-2-dimethylamino-1-phenyl-propyl ester

(3R,4E)-(-)-3-Hydroxy-5-phenyl-4-pentensaeure-methylester

methyl iodide

Downstream raw materials:

Methyl 2-methyl-3-oxo-5-phenyl-4-pentenoate

(E)-(2R,3S)-2-Methyl-5-phenyl-pent-4-ene-1,3-diol

(E)-(2S,3R)-3-Methoxy-2-methyl-5-phenyl-pent-4-enoic acid

(E)-(2S,3R)-3-Methoxy-2-methyl-5-phenyl-pent-4-enoic acid methyl ester