[2S,2(2R,5S,5(1R)),7S,8S,9R,10R]-9-triisopropylsilyloxy-7-(4-methoxy-benzyloxy)-8,10-dimethyl-2-[5-methyl-5-(1-(t-butyldimethylsilyloxy)-ethyl)tetrahydrofuran-2-yl]-2-trimethylsilyloxy-11-trityloxy-undecan-5-one

Base Information

• Chemical Name: [2S,2(2R,5S,5(1R)),7S,8S,9R,10R]-9-triisopropylsilyloxy-7-(4-methoxy-benzyloxy)-8,10-dimethyl-2-[5-methyl-5-(1-(t-butyldimethylsilyloxy)-ethyl)tetrahydrofuran-2-yl]-2-trimethylsilyloxy-11-trityloxy-undecan-5-one
• CAS No.: 440103-99-1
• Molecular Formula: C₆₅H₁₀₂O₈Si₃
• Molecular Weight: 1095.78
• Mol file: 440103-99-1.mol

Synonyms:[2S,2(2R,5S,5(1R)),7S,8S,9R,10R]-9-triisopropylsilyloxy-7-(4-methoxy-benzyloxy)-8,10-dimethyl-2-[5-methyl-5-(1-(t-butyldimethylsilyloxy)-ethyl)tetrahydrofuran-2-yl]-2-trimethylsilyloxy-11-trityloxy-undecan-5-one

Chemical Property of [2S,2(2R,5S,5(1R)),7S,8S,9R,10R]-9-triisopropylsilyloxy-7-(4-methoxy-benzyloxy)-8,10-dimethyl-2-[5-methyl-5-(1-(t-butyldimethylsilyloxy)-ethyl)tetrahydrofuran-2-yl]-2-trimethylsilyloxy-11-trityloxy-undecan-5-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [2S,2(2R,5S,5(1R)),7S,8S,9R,10R]-9-triisopropylsilyloxy-7-(4-methoxy-benzyloxy)-8,10-dimethyl-2-[5-methyl-5-(1-(t-butyldimethylsilyloxy)-ethyl)tetrahydrofuran-2-yl]-2-trimethylsilyloxy-11-trityloxy-undecan-5-one

There total 19 articles about [2S,2(2R,5S,5(1R)),7S,8S,9R,10R]-9-triisopropylsilyloxy-7-(4-methoxy-benzyloxy)-8,10-dimethyl-2-[5-methyl-5-(1-(t-butyldimethylsilyloxy)-ethyl)tetrahydrofuran-2-yl]-2-trimethylsilyloxy-11-trityloxy-undecan-5-one 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:

(2S,7S,8S,9R,10R)-4-Benzenesulfonyl-2-{(2R,5S)-5-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-methyl-tetrahydro-furan-2-yl}-7-(4-methoxy-benzyloxy)-8,10-dimethyl-9-triisopropylsilanyloxy-2-trimethylsilanyloxy-11-trityloxy-undecan-5-one (440103-98-0) → [2S,2(2R,5S,5(1R)),7S,8S,9R,10R]-9-triisopropylsilyloxy-7-(4-methoxy-benzyloxy)-8,10-dimethyl-2-[5-methyl-5-(1-(t-butyldimethylsilyloxy)-ethyl)tetrahydrofuran-2-yl]-2-trimethylsilyloxy-11-trityloxy-undecan-5-one (440103-99-1)

Guidance literature:

With samarium diiodide; In tetrahydrofuran; ethanol; at -78 ℃; for 0.5h;

DOI:10.1021/ol025872f

Reference yield:

[2E,6E]-9-benzenesulfonyl-3,7-dimethyl-nona-2,6-dien-1-ol (440104-18-7) → [2S,2(2R,5S,5(1R)),7S,8S,9R,10R]-9-triisopropylsilyloxy-7-(4-methoxy-benzyloxy)-8,10-dimethyl-2-[5-methyl-5-(1-(t-butyldimethylsilyloxy)-ethyl)tetrahydrofuran-2-yl]-2-trimethylsilyloxy-11-trityloxy-undecan-5-one (440103-99-1)

Guidance literature:

Multi-step reaction with 9 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

With pyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; n-butyllithium; perchloric acid; samarium diiodide; bis(acetylacetonate)oxovanadium; L-(+)-diisopropyl tartrate; 18-crown-6 ether; pyridinium p-toluenesulfonate; 4-methylmorpholine N-oxide; triethylamine; sodium iodide; tetrapropylammonium perruthennate; 4 A molecular sieve; In tetrahydrofuran; decane; ethanol; hexane; dichloromethane; water; butanone;

DOI:10.1021/ol025872f

Reference yield:

3-(6-benzenesulfonyl-4-methyl-hex-3-enyl)-3-methyl-oxiran-2-ylmethanol → [2S,2(2R,5S,5(1R)),7S,8S,9R,10R]-9-triisopropylsilyloxy-7-(4-methoxy-benzyloxy)-8,10-dimethyl-2-[5-methyl-5-(1-(t-butyldimethylsilyloxy)-ethyl)tetrahydrofuran-2-yl]-2-trimethylsilyloxy-11-trityloxy-undecan-5-one (440103-99-1)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 95 percent / pyridine / CH₂Cl₂ / 48 h / -10 °C

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

2.2: 67 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / -20 °C

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

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

4.2: 81 percent / tributyltin hydride; AIBN / toluene / 3 h / Heating

5.1: 93 percent / triethylamine / CH₂Cl₂ / 3 h / -78 °C

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

6.2: tetrahydrofuran; hexane / 0.5 h

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

8.1: 673 mg / samarium diiodide / ethanol; tetrahydrofuran / 0.5 h / -78 °C

With pyridine; tert.-butylhydroperoxide; n-butyllithium; perchloric acid; samarium diiodide; bis(acetylacetonate)oxovanadium; 18-crown-6 ether; pyridinium p-toluenesulfonate; 4-methylmorpholine N-oxide; triethylamine; sodium iodide; tetrapropylammonium perruthennate; 4 A molecular sieve; In tetrahydrofuran; decane; ethanol; hexane; dichloromethane; water; butanone;

DOI:10.1021/ol025872f

upstream raw materials:

(2S,7S,8S,9R,10R)-4-Benzenesulfonyl-2-{(2R,5S)-5-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-methyl-tetrahydro-furan-2-yl}-7-(4-methoxy-benzyloxy)-8,10-dimethyl-9-triisopropylsilanyloxy-2-trimethylsilanyloxy-11-trityloxy-undecan-5-one

[2E,6E]-9-benzenesulfonyl-3,7-dimethyl-nona-2,6-dien-1-ol

(2S)-4-(benzenesulfonyl)-2-[(2R,5S)-5-[(1R)-1-[(tert-butyldimethylsilyl)oxy]ethyl]-5-methyloxolan-2-yl]butan-2-ol

[2R,3S,6E]-toluene-4-sulfonic acid-9-benzenesulfonyl-2-(t-butyldimethylsiloxy)-3-hydroxy-3,7-dimethyl-non-6-enyl ester

Downstream raw materials:

[2S,2(2R,5S,5(1R)),7S,8S,9R,10R]-7-hydroxy-9-triisopropylsilyloxy-8,10-dimethyl-2-[5-methyl-5-(1-(t-butyldimethylsilyloxy)-ethyl)tetrahydrofuran-2-yl]-2-trimethylsilyloxy-11-trityloxy-undecan-5-one

ionomycin

benzoic acid 1-[2,5'-dimethyl-5'-(1-t-butyldimetylsilyloxy-ethyl)-octahydro-[2,2']bifuranyl-5-ylmethyl]-2,4-dimethyl-5-oxo-3-triisopropylsilyloxy-pentyl ester

[1S,1(2S,5S,2'R,5'S,5'(1R)),2S,3R,4R]-benzoic acid 1-[2,5'-dimethyl-5'-(1-t-butyldimethylsilyloxy-ethyl)-octahydro-[2,2']bifuranyl-5-ylmethyl]-5-hydroxy-2,4-dimethyl-3-triisopropylsilyloxy-pentyl ester