(1S)-2-Hydroxy-1,2,2-triphenylethyl (3S,5E)-5-ethyl-3-hydroxy-4,4-dimethyl-5-heptenoate

Base Information

• Chemical Name: (1S)-2-Hydroxy-1,2,2-triphenylethyl (3S,5E)-5-ethyl-3-hydroxy-4,4-dimethyl-5-heptenoate
• CAS No.: 210690-73-6
• Molecular Formula: C₃₁H₃₆O₄
• Molecular Weight: 472.624
• Mol file: 210690-73-6.mol

Synonyms:(1S)-2-Hydroxy-1,2,2-triphenylethyl (3S,5E)-5-ethyl-3-hydroxy-4,4-dimethyl-5-heptenoate

Chemical Property of (1S)-2-Hydroxy-1,2,2-triphenylethyl (3S,5E)-5-ethyl-3-hydroxy-4,4-dimethyl-5-heptenoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S)-2-Hydroxy-1,2,2-triphenylethyl (3S,5E)-5-ethyl-3-hydroxy-4,4-dimethyl-5-heptenoate

There total 7 articles about (1S)-2-Hydroxy-1,2,2-triphenylethyl (3S,5E)-5-ethyl-3-hydroxy-4,4-dimethyl-5-heptenoate 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: 75.0%

(S)-2-acetoxy-1,1,2-triphenylethanol (95061-51-1) + (E)-3-Ethyl-2,2-dimethyl-3-pentenal (210690-71-4) → (1S)-2-Hydroxy-1,2,2-triphenylethyl (3S,5E)-5-ethyl-3-hydroxy-4,4-dimethyl-5-heptenoate (210690-73-6)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; 1.) -78 deg C, 2.) -78 deg C, 90 min;

DOI:10.1055/s-1998-1794

Reference yield:

(S)-2-acetoxy-1,1,2-triphenylethanol (95061-51-1) + (E)-3-Ethyl-2,2-dimethyl-3-pentenal (210690-71-4) → (1S)-2-Hydroxy-1,2,2-triphenylethyl (3S,5E)-5-ethyl-3-hydroxy-4,4-dimethyl-5-heptenoate (210690-73-6) + (1S)-2-Hydroxy-1,2,2-triphenylethyl (3R,5E)-5-ethyl-3-hydroxy-4,4-dimethyl-5-heptenoate

Guidance literature:

(S)-2-acetoxy-1,1,2-triphenylethanol; With lithium diisopropyl amide; In tetrahydrofuran; hexane; at 0 ℃; for 1h;

(E)-3-Ethyl-2,2-dimethyl-3-pentenal; In tetrahydrofuran; hexane; at -78 ℃; for 1.5h; Title compound not separated from byproducts;

DOI:10.1002/(SICI)1521-3765(19990903)5:9<2483::AID-CHEM2483>3.0.CO;2-N

Reference yield:

(E)-3-Ethyl-2,2-dimethyl-3-penten-1-ol (210690-97-4) → (1S)-2-Hydroxy-1,2,2-triphenylethyl (3S,5E)-5-ethyl-3-hydroxy-4,4-dimethyl-5-heptenoate (210690-73-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: DMSO; (COCl)2; NEt₃ / CH₂Cl₂ / 1.75 h / -70 - 20 °C

2.1: LDA / tetrahydrofuran; hexane / 1 h / 0 °C

2.2: tetrahydrofuran; hexane / 1.5 h / -78 °C

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; 1.1: Oxidation / 2.1: Metallation / 2.2: Condensation;

DOI:10.1002/(SICI)1521-3765(19990903)5:9<2483::AID-CHEM2483>3.0.CO;2-N

upstream raw materials:

(S)-2-acetoxy-1,1,2-triphenylethanol

(E)-3-Ethyl-2,2-dimethyl-3-pentenal

(E)-3-Ethyl-2,2-dimethyl-3-penten-1-ol

Ethyl (E)-3-ethyl-2,2-dimethyl-3-pentenoate

Downstream raw materials:

(7S,10R,11S,12S,19S,Z)-7,11-bis(tert-butyldimethylsilyloxy)-2,2,3,3,8,8,10,12,16,21,21,22,22-tridecamethyl-19-((E)-1-(2-methylthiazol-4-yl)prop-1-en-2-yl)-4,20-dioxa-3,21-disilatricos-16-en-9-one