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

Base Information

• Chemical Name: 2-Octenoic acid, 4,8-bis[[(1,1-dimethylethyl)diphenylsilyl]oxy]-7-hydroxy-, (1S,2R)-2-(1-methyl-1-phenylethyl)cyclohexyl ester, (2Z,4R,7S)-
• CAS No.: 837428-23-6
• Molecular Formula: C55H70O5Si2
• Molecular Weight: 867.329
• Mol file: 837428-23-6.mol

Synonyms:

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

There total 4 articles about 2-Octenoic acid, 4,8-bis[[(1,1-dimethylethyl)diphenylsilyl]oxy]-7-hydroxy-, (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: 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: 70.0%

(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 dmap; In ethanol; Heating;

DOI:10.1021/ol0479242

Reference yield:

meso-(2R,5S)-2,5-bis(tert-butyldiphenylsilyloxy)hexane-1,6-dial (134341-56-3) → (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:

Multi-step reaction with 3 steps

1: 77 percent / NaHMDS / tetrahydrofuran; toluene / 4 h / -78 °C

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

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

With dmap; sodium tetrahydroborate; sodium hexamethyldisilazane; In tetrahydrofuran; ethanol; isopropyl alcohol; toluene; 1: Horner-Wadsworth-Emmons reaction;

DOI:10.1021/jo052233k

upstream raw materials:

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

(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

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

Downstream raw materials:

[3-(tert-butyl-diphenyl-silanyloxy)-6-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-pyran-2-yl]-acetaldehyde

(5S)-3-{(2R,8R,13R)-13-{[tert-butyl(dimethyl)silyl]oxy}-13-[(2R,5R,6R)-5-{[tert-butyl(diphenyl)silyl]oxy}-6-dodecyltetrahydro-2H-pyran-2-yl]-8-hydroxy-2-[2-(trimethylsilyl)ethoxy]tridecyl}-5-methylfuran-2(5H)-one

(5S)-3-{(2R,8R,11E,13R)-13-{[tert-butyl(dimethyl)silyl]oxy}-13-{(2R,5R,6R)-5-{[tert-butyl(diphenyl)silyl]oxy}-6-[(E)-dodec-2-en-1-yl]tetrahydro-2H-pyran-2-yl}-8-hydroxy-2-[2-(trimethylsilyl)ethoxy]tridec-11-en-9-yn-1-yl}-5-methylfuran-2(5H)-one

{(2R,3R,6R)-3-{[tert-butyl(diphenyl)silyl]oxy}-6-{[tert-butyl(diphenyl)silyl]oxymethyl}-tetrahydro-2H-pyran-2-yl}-acetic acid (1S,2R)-2-(1-methyl-1-phenylethyl)cyclohexyl ester