[1S,1(2S,5S,2'R,5'S,5'(1R)),2S,3R,4R,5E,8R,10R]-benzoic acid 1-[5'-(1-t-butyldimethylsilyloxy-ethyl)-2,5'-dimethyl-octahydro-[2,2']bifuranyl-5-yl-methyl]-11-hydroxy-2,4,8,10-tetramethyl-3-triisopropylsilyloxy-undec-5-enyl ester

Base Information

• Chemical Name: [1S,1(2S,5S,2'R,5'S,5'(1R)),2S,3R,4R,5E,8R,10R]-benzoic acid 1-[5'-(1-t-butyldimethylsilyloxy-ethyl)-2,5'-dimethyl-octahydro-[2,2']bifuranyl-5-yl-methyl]-11-hydroxy-2,4,8,10-tetramethyl-3-triisopropylsilyloxy-undec-5-enyl ester
• CAS No.: 440104-05-2
• Molecular Formula: C₅₀H₉₀O₇Si₂
• Molecular Weight: 859.431
• Mol file: 440104-05-2.mol

Synonyms:[1S,1(2S,5S,2'R,5'S,5'(1R)),2S,3R,4R,5E,8R,10R]-benzoic acid 1-[5'-(1-t-butyldimethylsilyloxy-ethyl)-2,5'-dimethyl-octahydro-[2,2']bifuranyl-5-yl-methyl]-11-hydroxy-2,4,8,10-tetramethyl-3-triisopropylsilyloxy-undec-5-enyl ester

Chemical Property of [1S,1(2S,5S,2'R,5'S,5'(1R)),2S,3R,4R,5E,8R,10R]-benzoic acid 1-[5'-(1-t-butyldimethylsilyloxy-ethyl)-2,5'-dimethyl-octahydro-[2,2']bifuranyl-5-yl-methyl]-11-hydroxy-2,4,8,10-tetramethyl-3-triisopropylsilyloxy-undec-5-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [1S,1(2S,5S,2'R,5'S,5'(1R)),2S,3R,4R,5E,8R,10R]-benzoic acid 1-[5'-(1-t-butyldimethylsilyloxy-ethyl)-2,5'-dimethyl-octahydro-[2,2']bifuranyl-5-yl-methyl]-11-hydroxy-2,4,8,10-tetramethyl-3-triisopropylsilyloxy-undec-5-enyl ester

There total 41 articles about [1S,1(2S,5S,2'R,5'S,5'(1R)),2S,3R,4R,5E,8R,10R]-benzoic acid 1-[5'-(1-t-butyldimethylsilyloxy-ethyl)-2,5'-dimethyl-octahydro-[2,2']bifuranyl-5-yl-methyl]-11-hydroxy-2,4,8,10-tetramethyl-3-triisopropylsilyloxy-undec-5-enyl ester 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: 97.0%

[1S,1(2S,5S,2'R,5'S,5'(1R)),2S,3R,4R,5E,8R,10R]-benzoic acid 1-[5'-(1-t-butyldimethylsilyloxy-ethyl)-2,5'-dimethyl-octahydro-[2,2']bifuranyl-5-yl-methyl]-11-(4-methoxy-benzyloxy)-2,4,8,10-tetramethyl-3-triisopropylsilyloxy-undec-5-enyl ester (440104-04-1) → [1S,1(2S,5S,2'R,5'S,5'(1R)),2S,3R,4R,5E,8R,10R]-benzoic acid 1-[5'-(1-t-butyldimethylsilyloxy-ethyl)-2,5'-dimethyl-octahydro-[2,2']bifuranyl-5-yl-methyl]-11-hydroxy-2,4,8,10-tetramethyl-3-triisopropylsilyloxy-undec-5-enyl ester (440104-05-2)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; at 0 ℃; for 2h;

DOI:10.1021/ol025872f

Reference yield:

[2E,6E]-9-benzenesulfonyl-3,7-dimethyl-nona-2,6-dien-1-ol (440104-18-7) → [1S,1(2S,5S,2'R,5'S,5'(1R)),2S,3R,4R,5E,8R,10R]-benzoic acid 1-[5'-(1-t-butyldimethylsilyloxy-ethyl)-2,5'-dimethyl-octahydro-[2,2']bifuranyl-5-yl-methyl]-11-hydroxy-2,4,8,10-tetramethyl-3-triisopropylsilyloxy-undec-5-enyl ester (440104-05-2)

Guidance literature:

Multi-step reaction with 18 steps

1.1: (+)-diisopropyl tartrate; titanium isopropoxide; tert-butyl hydroperoxide / CH₂Cl₂; decane / -20 °C

2.1: 95 percent / pyridine / CH₂Cl₂ / 48 h / -10 °C

3.1: perchloric acid / tetrahydrofuran; H₂O / 2 h / Heating

3.2: 67 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / -20 °C

4.1: vanadil acetylacetonate; t-butyl hydroperoxide; pyridinium para-toluenesulfonate / 4 Angstroem molecular sieve / various solvent(s); CH₂Cl₂; decane / 29 h / 20 °C

5.1: sodium iodide; 18-c-6 / butan-2-one / Heating

5.2: 81 percent / tributyltin hydride; AIBN / toluene / 3 h / Heating

6.1: 93 percent / triethylamine / CH₂Cl₂ / 3 h / -78 °C

7.1: n-butyl lithium / tetrahydrofuran; hexane / 0.5 h / -78 °C

7.2: tetrahydrofuran; hexane / 0.5 h

8.1: N-methylmorpholine N-oxide / tetrapropylammonium perruthenate / CH₂Cl₂ / 2 h / 20 °C

9.1: 673 mg / samarium diiodide / ethanol; tetrahydrofuran / 0.5 h / -78 °C

10.1: 86 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / H₂O; CH₂Cl₂ / 1 h / 0 °C

11.1: 90 percent / samarium diiodide / tetrahydrofuran / 0.5 h / 0 °C

12.1: 4-dimethylaminopyridine / CH₂Cl₂

13.1: HCl / tetrahydrofuran / 5 h / 0 °C

14.1: 264 mg / sodium hydride / tetrahydrofuran / 0.33 h / 50 °C

15.1: 96 percent / Pd(OH)2 / ethanol; cyclohexane / 12 h / Heating

16.1: 91 percent / N-methylmorpholine N-oxide / tetrapropylammonium perruthenate / CH₂Cl₂ / 0.5 h / 20 °C

17.1: potassium hexamethyldisilazide / tetrahydrofuran; toluene / 0.5 h

17.2: 85 percent / tetrahydrofuran; toluene / -78 - 20 °C

18.1: 97 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / H₂O; CH₂Cl₂ / 2 h / 0 °C

With pyridine; titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; dmap; n-butyllithium; perchloric acid; samarium diiodide; bis(acetylacetonate)oxovanadium; L-(+)-diisopropyl tartrate; 18-crown-6 ether; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; sodium hydride; 4-methylmorpholine N-oxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium iodide; palladium dihydroxide; tetrapropylammonium perruthennate; 4 A molecular sieve; In tetrahydrofuran; decane; ethanol; hexane; dichloromethane; cyclohexane; water; toluene; butanone; 11.1: Tishchenko reaction / 17.1: Julia reaction;

DOI:10.1021/ol025872f

Reference yield:

(2S)-4-(benzenesulfonyl)-2-[(2R,5S)-5-[(1R)-1-[(tert-butyldimethylsilyl)oxy]ethyl]-5-methyloxolan-2-yl]butan-2-ol (440104-23-4) → [1S,1(2S,5S,2'R,5'S,5'(1R)),2S,3R,4R,5E,8R,10R]-benzoic acid 1-[5'-(1-t-butyldimethylsilyloxy-ethyl)-2,5'-dimethyl-octahydro-[2,2']bifuranyl-5-yl-methyl]-11-hydroxy-2,4,8,10-tetramethyl-3-triisopropylsilyloxy-undec-5-enyl ester (440104-05-2)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 93 percent / triethylamine / CH₂Cl₂ / 3 h / -78 °C

2.1: n-butyl lithium / tetrahydrofuran; hexane / 0.5 h / -78 °C

2.2: tetrahydrofuran; hexane / 0.5 h

3.1: N-methylmorpholine N-oxide / tetrapropylammonium perruthenate / CH₂Cl₂ / 2 h / 20 °C

4.1: 673 mg / samarium diiodide / ethanol; tetrahydrofuran / 0.5 h / -78 °C

5.1: 86 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / H₂O; CH₂Cl₂ / 1 h / 0 °C

6.1: 90 percent / samarium diiodide / tetrahydrofuran / 0.5 h / 0 °C

7.1: 4-dimethylaminopyridine / CH₂Cl₂

8.1: HCl / tetrahydrofuran / 5 h / 0 °C

9.1: 264 mg / sodium hydride / tetrahydrofuran / 0.33 h / 50 °C

10.1: 96 percent / Pd(OH)2 / ethanol; cyclohexane / 12 h / Heating

11.1: 91 percent / N-methylmorpholine N-oxide / tetrapropylammonium perruthenate / CH₂Cl₂ / 0.5 h / 20 °C

12.1: potassium hexamethyldisilazide / tetrahydrofuran; toluene / 0.5 h

12.2: 85 percent / tetrahydrofuran; toluene / -78 - 20 °C

13.1: 97 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / H₂O; CH₂Cl₂ / 2 h / 0 °C

With hydrogenchloride; dmap; n-butyllithium; samarium diiodide; potassium hexamethylsilazane; sodium hydride; 4-methylmorpholine N-oxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium dihydroxide; tetrapropylammonium perruthennate; In tetrahydrofuran; ethanol; hexane; dichloromethane; cyclohexane; water; toluene; 6.1: Tishchenko reaction / 12.1: Julia reaction;

DOI:10.1021/ol025872f

upstream raw materials:

[1S,1(2S,5S,2'R,5'S,5'(1R)),2S,3R,4R,5E,8R,10R]-benzoic acid 1-[5'-(1-t-butyldimethylsilyloxy-ethyl)-2,5'-dimethyl-octahydro-[2,2']bifuranyl-5-yl-methyl]-11-(4-methoxy-benzyloxy)-2,4,8,10-tetramethyl-3-triisopropylsilyloxy-undec-5-enyl ester

[3S,5R]-6-(4-methoxy-benzyloxy)-3,5-dimethyl-hexanal

[3S,5R]-6-(4-methoxy-benzyloxy)-3,5-dimethyl-hexanenitrile

[3S,5R]-6-(4-methoxy-benzyloxy)-3,5-dimethyl-hexan-1-ol

Downstream raw materials:

Benzoic acid (E)-(1S,2S,3R,4R,8R,10R)-1-{(2S,5S,2'R,5'S)-5'-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2,5'-dimethyl-octahydro-[2,2']bifuranyl-5-ylmethyl}-2,4,8,10-tetramethyl-11-oxo-3-triisopropylsilanyloxy-undec-5-enyl ester

[1S,1(2S,5S,2'R,5'S,5'(1R)),2S,3R,4R,5E,8R,10R,14S,16S,18S]-benzoic acid 1-[5'-(1-TBDMS-ethyl)-2,5'-dimethyl-octahydro[2,2']bifuranyl-5-yl-methyl]-20-methoxycarbonyl-2,4,8,10,14,16,18-heptamethyl-11,13-dioxo-3-triisopropylsilyloxy-eicos-5-enyl ester

benzoic acid 3-hydroxy-1-[5'-(1-hydroxy-ethyl)-2,5'-dimethyl-octahydro-[2,2']bifuranyl-5-yl-methyl]-20-methoxycarbonyl-2,4,8,10,14,16,18-heptamethyl-11,13-dioxo-eicos-5-enyl ester

ionomycin