(S,E)-9-(tert-butyldiphenylsilyloxy)-11-((4S,5S)-2,2-dimethyl-5-pentyl-1,3-dioxolan-4-yl)undec-10-enoic acid

Base Information

• Chemical Name: (S,E)-9-(tert-butyldiphenylsilyloxy)-11-((4S,5S)-2,2-dimethyl-5-pentyl-1,3-dioxolan-4-yl)undec-10-enoic acid
• CAS No.: 935746-75-1
• Molecular Formula: C₃₇H₅₆O₅Si
• Molecular Weight: 608.934
• Mol file: 935746-75-1.mol

Synonyms:(S,E)-9-(tert-butyldiphenylsilyloxy)-11-((4S,5S)-2,2-dimethyl-5-pentyl-1,3-dioxolan-4-yl)undec-10-enoic acid

Chemical Property of (S,E)-9-(tert-butyldiphenylsilyloxy)-11-((4S,5S)-2,2-dimethyl-5-pentyl-1,3-dioxolan-4-yl)undec-10-enoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S,E)-9-(tert-butyldiphenylsilyloxy)-11-((4S,5S)-2,2-dimethyl-5-pentyl-1,3-dioxolan-4-yl)undec-10-enoic acid

There total 17 articles about (S,E)-9-(tert-butyldiphenylsilyloxy)-11-((4S,5S)-2,2-dimethyl-5-pentyl-1,3-dioxolan-4-yl)undec-10-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:

(S,E)-9-(tert-butyldiphenylsilyloxy)-11-((4S,5S)-2,2-dimethyl-5-pentyl-1,3-dioxolan-4-yl)undec-10-en-1-ol (935746-74-0) → (S,E)-9-(tert-butyldiphenylsilyloxy)-11-((4S,5S)-2,2-dimethyl-5-pentyl-1,3-dioxolan-4-yl)undec-10-enoic acid (935746-75-1)

Guidance literature:

(S,E)-9-(tert-butyldiphenylsilyloxy)-11-((4S,5S)-2,2-dimethyl-5-pentyl-1,3-dioxolan-4-yl)undec-10-en-1-ol; With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 - -60 ℃;

With sodium chlorite; sodium dihydrogenphosphate; In dimethyl sulfoxide; at 20 ℃;

DOI:10.1016/j.tetlet.2007.01.163

Reference yield:

(E)-ethyl 11-(4-methoxybenzyloxy)undec-2-enoate (935746-64-8) → (S,E)-9-(tert-butyldiphenylsilyloxy)-11-((4S,5S)-2,2-dimethyl-5-pentyl-1,3-dioxolan-4-yl)undec-10-enoic acid (935746-75-1)

Guidance literature:

Multi-step reaction with 12 steps

1: 96 percent / K₃Fe(CN)6; aq. K₂CO₃; MeSO₂NH₂ / OsO₄; (DHQ)2PHAL / 2-methyl-propan-2-ol; toluene / 24 h / 0 °C

2: 94 percent / TsOH / CH₂Cl₂ / 20 °C

3: 95 percent / DIBAL-H / CH₂Cl₂; toluene / 2 h / 0 - 20 °C

4: 89 percent / N-chlorosuccinimide; PPh₃ / CH₂Cl₂ / 3 h / 0 - 20 °C

5: 82 percent / n-BuLi; HMPA / tetrahydrofuran; hexane / -42 - 20 °C

6: 98 percent / imidazole / CH₂Cl₂ / 0 °C

7: 86 percent / CuI; Et₃N / Pd(PPh₃)2Cl₂ / 6 h

8: 91 percent / K₃Fe(CN)6; aq. K₂CO₃; MeSO₂NH₂ / OsO₄; (DHQ)2PHAL / 2-methyl-propan-2-ol; toluene / 24 h / 0 °C

9: 90 percent / Li; liq. NH₃ / tetrahydrofuran / 1 h / -78 °C

10: 92 percent / TsOH / CH₂Cl₂ / 20 °C

11: IBX / ethyl acetate / 5 h / Heating

12: 174 mg / aq. NaClO₂; NaH₂PO₄ / dimethylsulfoxide / 20 °C

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium chlorite; sodium dihydrogenphosphate; N-chloro-succinimide; copper(l) iodide; n-butyllithium; methanesulfonamide; ammonia; lithium; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; triethylamine; triphenylphosphine; potassium hexacyanoferrate(III); 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; bis-triphenylphosphine-palladium(II) chloride; osmium(VIII) oxide; Hydroquinone 1,4-phthalazinediyl diether; In tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide; ethyl acetate; toluene; tert-butyl alcohol; 1: Sharpless asymmetric dihydroxylation / 7: Sonogashira coupling / 8: Sharpless asymmetric dihydroxylation / 9: Birch reduction;

DOI:10.1016/j.tet.2007.05.047

Reference yield:

(S)-11-(4-methoxybenzyloxy)undec-1-yn-3-ol (935746-69-3) → (S,E)-9-(tert-butyldiphenylsilyloxy)-11-((4S,5S)-2,2-dimethyl-5-pentyl-1,3-dioxolan-4-yl)undec-10-enoic acid (935746-75-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 98 percent / imidazole / CH₂Cl₂ / 0 °C

2: 86 percent / CuI; Et₃N / Pd(PPh₃)2Cl₂ / 6 h

3: 91 percent / K₃Fe(CN)6; aq. K₂CO₃; MeSO₂NH₂ / OsO₄; (DHQ)2PHAL / 2-methyl-propan-2-ol; toluene / 24 h / 0 °C

4: 90 percent / Li; liq. NH₃ / tetrahydrofuran / 1 h / -78 °C

5: 92 percent / TsOH / CH₂Cl₂ / 20 °C

6: IBX / ethyl acetate / 5 h / Heating

7: 174 mg / aq. NaClO₂; NaH₂PO₄ / dimethylsulfoxide / 20 °C

With 1H-imidazole; sodium chlorite; sodium dihydrogenphosphate; copper(l) iodide; methanesulfonamide; ammonia; lithium; potassium carbonate; toluene-4-sulfonic acid; triethylamine; potassium hexacyanoferrate(III); 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; bis-triphenylphosphine-palladium(II) chloride; osmium(VIII) oxide; Hydroquinone 1,4-phthalazinediyl diether; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; ethyl acetate; toluene; tert-butyl alcohol; 2: Sonogashira coupling / 3: Sharpless asymmetric dihydroxylation / 4: Birch reduction;

DOI:10.1016/j.tet.2007.05.047

upstream raw materials:

(S,E)-9-(tert-butyldiphenylsilyloxy)-11-((4S,5S)-2,2-dimethyl-5-pentyl-1,3-dioxolan-4-yl)undec-10-en-1-ol

C₃₄H₅₄SiO₄C₃H₂

(S)-11-(4-methoxybenzyloxy)undec-1-yn-3-ol

(E)-ethyl 11-(4-methoxybenzyloxy)undec-2-enoate

Downstream raw materials:

(9S,10E,12S,13S)-(-)-9,12,13-trihydroxy-10-octadecenoic acid