(Z)-(4S,5S,6S)-7-(tert-Butyl-diphenyl-silanyloxy)-5-hydroxy-4,6-dimethyl-hept-2-enoic acid

Base Information

• Chemical Name: (Z)-(4S,5S,6S)-7-(tert-Butyl-diphenyl-silanyloxy)-5-hydroxy-4,6-dimethyl-hept-2-enoic acid
• CAS No.: 235099-37-3
• Molecular Formula: C₂₅H₃₄O₄Si
• Molecular Weight: 426.628
• Mol file: 235099-37-3.mol

Synonyms:(Z)-(4S,5S,6S)-7-(tert-Butyl-diphenyl-silanyloxy)-5-hydroxy-4,6-dimethyl-hept-2-enoic acid

Chemical Property of (Z)-(4S,5S,6S)-7-(tert-Butyl-diphenyl-silanyloxy)-5-hydroxy-4,6-dimethyl-hept-2-enoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-(4S,5S,6S)-7-(tert-Butyl-diphenyl-silanyloxy)-5-hydroxy-4,6-dimethyl-hept-2-enoic acid

There total 3 articles about (Z)-(4S,5S,6S)-7-(tert-Butyl-diphenyl-silanyloxy)-5-hydroxy-4,6-dimethyl-hept-2-enoic acid 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:

(4S,5S,6S)-7-(tert-Butyl-diphenyl-silanyloxy)-5-hydroxy-4,6-dimethyl-hept-2-ynoic acid (235099-36-2) → (Z)-(4S,5S,6S)-7-(tert-Butyl-diphenyl-silanyloxy)-5-hydroxy-4,6-dimethyl-hept-2-enoic acid (235099-37-3)

Guidance literature:

With quinoline; hydrogen; Pd-BaSO₄; In ethanol; for 1h;

DOI:10.1021/jo9823083

Reference yield:

(2S)-3-{[tert-butyl(diphenyl)silyl]oxy}-2-methylpropanal (92817-88-4) → (Z)-(4S,5S,6S)-7-(tert-Butyl-diphenyl-silanyloxy)-5-hydroxy-4,6-dimethyl-hept-2-enoic acid (235099-37-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 70 percent / Pd(OAc)2, PPh₃, Et₂Zn / tetrahydrofuran; hexane / 24 h / -20 °C

2: 400 mg / n-BuLi / tetrahydrofuran; hexane / 0.25 h / -40 °C

3: quinoline, H₂ / 5 percent Pd/BaSO₄ / ethanol / 1 h

With quinoline; palladium diacetate; n-butyllithium; hydrogen; diethylzinc; triphenylphosphine; Pd-BaSO₄; In tetrahydrofuran; ethanol; hexane;

DOI:10.1021/jo9823083

Reference yield:

(2S,3S,4S)-(+)-1-<(tert-butyldiphenylsilyl)oxy>-2,4-dimethyl-5-hexyn-3-ol (227792-06-5) → (Z)-(4S,5S,6S)-7-(tert-Butyl-diphenyl-silanyloxy)-5-hydroxy-4,6-dimethyl-hept-2-enoic acid (235099-37-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 400 mg / n-BuLi / tetrahydrofuran; hexane / 0.25 h / -40 °C

2: quinoline, H₂ / 5 percent Pd/BaSO₄ / ethanol / 1 h

With quinoline; n-butyllithium; hydrogen; Pd-BaSO₄; In tetrahydrofuran; ethanol; hexane;

DOI:10.1021/jo9823083

upstream raw materials:

(4S,5S,6S)-7-(tert-Butyl-diphenyl-silanyloxy)-5-hydroxy-4,6-dimethyl-hept-2-ynoic acid

(2S)-3-{[tert-butyl(diphenyl)silyl]oxy}-2-methylpropanal

(2S,3S,4S)-(+)-1-<(tert-butyldiphenylsilyl)oxy>-2,4-dimethyl-5-hexyn-3-ol

Downstream raw materials:

(5S,6S)-6-{(1S)-2-[(tert-butyldiphenylsilyl)oxy]-1-methylethyl}-5-methyl-5,6-dihydro-2H-pyran-2-one