2-Octenoic acid, 4,7-bis[[(1,1-dimethylethyl)diphenylsilyl]oxy]-8-oxo-, (1S,2R)-2-(1-methyl-1-phenylethyl)cyclohexyl ester, (2Z,4R,7S)-

Base Information

• Chemical Name: 2-Octenoic acid, 4,7-bis[[(1,1-dimethylethyl)diphenylsilyl]oxy]-8-oxo-, (1S,2R)-2-(1-methyl-1-phenylethyl)cyclohexyl ester, (2Z,4R,7S)-
• CAS No.: 837428-48-5
• Molecular Formula: C55H68O5Si2
• Molecular Weight: 865.313
• Mol file: 837428-48-5.mol

Synonyms:

Chemical Property of 2-Octenoic acid, 4,7-bis[[(1,1-dimethylethyl)diphenylsilyl]oxy]-8-oxo-, (1S,2R)-2-(1-methyl-1-phenylethyl)cyclohexyl ester, (2Z,4R,7S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-Octenoic acid, 4,7-bis[[(1,1-dimethylethyl)diphenylsilyl]oxy]-8-oxo-, (1S,2R)-2-(1-methyl-1-phenylethyl)cyclohexyl ester, (2Z,4R,7S)-

There total 1 articles about 2-Octenoic acid, 4,7-bis[[(1,1-dimethylethyl)diphenylsilyl]oxy]-8-oxo-, (1S,2R)-2-(1-methyl-1-phenylethyl)cyclohexyl ester, (2Z,4R,7S)- 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: 77.0%

meso-(2R,5S)-2,5-bis(tert-butyldiphenylsilyloxy)hexane-1,6-dial (134341-56-3) + [Bis-(2,2,2-trifluoro-ethoxy)-phosphoryl]-acetic acid (1S,2R)-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester → (1S,2R)-2-(1-methyl-1-phenylethyl)cyclohexyl (2Z,4R,7S)-4,8-bis{[tert-butyl(diphenyl)silyl]oxy}-8-oxooct-2-enoate (837428-48-5)

Guidance literature:

With sodium hexamethyldisilazane; In tetrahydrofuran; toluene; at -78 ℃; for 4h;

DOI:10.1021/ol0479242 DOI:10.1021/jo052233k

Reference yield: 70.0%

(1S,2R)-2-(1-methyl-1-phenylethyl)cyclohexyl (2Z,4R,7S)-4,8-bis{[tert-butyl(diphenyl)silyl]oxy}-8-oxooct-2-enoate (837428-48-5) → (Z)-(4R,7S)-4,7-Bis-(tert-butyl-diphenyl-silanyloxy)-8-hydroxy-oct-2-enoic acid (1S,2R)-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester (837428-26-9) + (1S,2R)-2-(1-methyl-1-phenylethyl)cyclohexyl (2Z,4R,7S)-4,8-bis{[tert-butyl(diphenyl)silyl]oxy}-7-hydroxyoct-2-enoate (837428-23-6)

Guidance literature:

With sodium tetrahydroborate; In isopropyl alcohol; at 0 ℃;

DOI:10.1021/ol0479242

Reference yield:

(1S,2R)-2-(1-methyl-1-phenylethyl)cyclohexyl (2Z,4R,7S)-4,8-bis{[tert-butyl(diphenyl)silyl]oxy}-8-oxooct-2-enoate (837428-48-5) → (S)-3-[(R)-7-{5-[(2R,5R,6R)-5-(tert-Butyl-diphenyl-silanyloxy)-6-tetradecyl-tetrahydro-pyran-2-yl]-tetrahydro-furan-2-yl}-2-(2-trimethylsilanyl-ethoxy)-heptyl]-5-methyl-5H-furan-2-one

Guidance literature:

Multi-step reaction with 11 steps

1.1: NaBH₄ / tetrahydrofuran; propan-2-ol / 3 h / 0 °C

2.1: DMAP / ethanol; various solvent(s) / 14 h / Heating

3.1: 95 percent / PPh₃; DIAD / toluene / 3 h / 20 °C

4.1: aq. LiOH / tetrahydrofuran / 2.5 h / 0 °C

4.2: t-BuOK / toluene / 0.83 h / 0 °C

5.1: t-BuOK / toluene / 0 °C

6.1: DIBAL-H / CH₂Cl₂; toluene / 0.25 h / -78 °C

6.2: 78 percent / NaHMDS / CH₂Cl₂; toluene; tetrahydrofuran / 12 h / -78 - 0 °C

7.1: 81 percent / Al₂O₃ / hexane / 24 h / 20 °C

8.1: 83 percent / Dess-Martin periodinane / CH₂Cl₂ / 4 h / 0 °C

9.1: Zn(OTf)2; (1S,2R)-N-methylephedrine; Et₃N / toluene / 60 °C

10.1: H₂ / Pd/C / methanol / 20 °C

11.1: ClCOCCl₃; Et₃N / CH₂Cl₂ / 0 - 20 °C

11.2: aq. NaHCO₃

With dmap; aluminum oxide; lithium hydroxide; sodium tetrahydroborate; di-isopropyl azodicarboxylate; (1S,2R)-(+)-N-methylephedrine; potassium tert-butylate; hydrogen; zinc trifluoromethanesulfonate; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; triphenylphosphine; trifluoroacetyl chloride; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; isopropyl alcohol; toluene; 3.1: Mitsunobu reaction / 6.2: Wittig reaction / 8.1: Dess-Martin oxidation;

DOI:10.1021/jo052233k

upstream raw materials:

meso-(2R,5S)-2,5-bis(tert-butyldiphenylsilyloxy)hexane-1,6-dial

Downstream raw materials:

(Z)-(4R,7S)-4,7-Bis-(tert-butyl-diphenyl-silanyloxy)-8-hydroxy-oct-2-enoic acid (1S,2R)-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester

(1S,2R)-2-(1-methyl-1-phenylethyl)cyclohexyl (2Z,4R,7S)-4,8-bis{[tert-butyl(diphenyl)silyl]oxy}-7-hydroxyoct-2-enoate

5-{[tert-butyl(diphenyl)silyl]oxy}-6-[(Z)-tetradec-2-enyl]tetrahydro-2H-pyran-2-carbaldehyde

[5-{[tert-butyl(diphenyl)silyl]oxy}-6-[(Z)-tetradec-2-enyl]tetrahydro-2H-pyran-2-yl]methanol