C₄₀H₅₆O₉Si

Base Information

• Chemical Name: C₄₀H₅₆O₉Si
• CAS No.: 208454-74-4
• Molecular Formula: C₄₀H₅₆O₉Si
• Molecular Weight: 708.965

Synonyms:C₄₀H₅₆O₉Si

Chemical Property of C₄₀H₅₆O₉Si

Chemical Property:

Purity/Quality:

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Technology Process of C₄₀H₅₆O₉Si

There total 19 articles about C₄₀H₅₆O₉Si 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:

tert-butylchlorodiphenylsilane (58479-61-1) + C24H38O9 → C40H56O9Si (208454-74-4)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 0 ℃; for 0.5h;

DOI:10.1021/jo990989b

Reference yield:

((2R,3S)-3-Allyloxy-tetrahydro-pyran-2-yl)-acetaldehyde (208454-48-2) → C40H56O9Si (208454-74-4)

Guidance literature:

Multi-step reaction with 18 steps

2.1: sec-butyllithium / tetrahydrofuran / -78 °C

2.2: 32 percent / tetrahydrofuran / -78 °C

3.1: 29 percent / TiCl₄; triphenylphosphine / CH₂Cl₂ / -78 - 0 °C

4.1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

5.1: N-methylmorpholine N-oxide; OsO₄ / H₂O; 2-methyl-propan-2-ol; various solvent(s) / 20 °C

6.1: lead tetraacetate / benzene / 0.5 h / 20 °C

7.1: 2.778 g / tetrahydrofuran; diethyl ether / -78 - 0 °C

8.1: 94 percent / oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / -78 - 20 °C

9.1: lithium diisopropylamide / tetrahydrofuran; hexane / 0.33 h / -78 °C

9.2: tetrahydrofuran; hexane / 0.33 h / -78 °C

10.1: N-bromosuccinimide / tetrahydrofuran / 0.75 h / 0 °C

11.1: 101.0 mg / camphorsulfonic acid / CH₂Cl₂; methanol / 0 - 20 °C

12.1: triethylamine; sulfur trioxide-pyridine complex / CH₂Cl₂; dimethylsulfoxide / 0.67 h / 0 °C

13.1: SmI₂ / tetrahydrofuran / 0.75 h / -78 °C

13.2: 4-(dimethylamino)pyridine / tetrahydrofuran / 0.5 h / 0 °C

14.1: 389.8 mg / sodium borohydride / CH₂Cl₂; methanol / 0.17 h / 0 °C

15.1: 300 mg / 4-(dimethylamino)pyridine / acetonitrile / 23 h / 20 °C

16.1: 26 percent / Bu₃SnH; azobis(isobutyronitrile) / toluene / 80 °C

17.1: tetra-n-butylammonium fluoride / tetrahydrofuran / 20 °C

18.1: 236 mg / imidazole / dimethylformamide / 0.5 h / 0 °C

With 1H-imidazole; 2,6-dimethylpyridine; lead(IV) acetate; dmap; sodium tetrahydroborate; N-Bromosuccinimide; osmium(VIII) oxide; samarium diiodide; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; sec.-butyllithium; tri-n-butyl-tin hydride; sulfur trioxide pyridine complex; titanium tetrachloride; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; triphenylphosphine; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol; benzene; 2.1: Metallation / 2.2: allylsilylation / 3.1: Cyclization / 4.1: Etherification / 5.1: Oxidation / 6.1: Oxidation / 7.1: Addition / 8.1: Oxidation / 9.1: Metallation / 9.2: Etherification / 10.1: Bromination / 11.1: Hydrolysis / 12.1: Oxidation / 13.1: Cyclization / 13.2: Acetylation / 14.1: Reduction / 15.1: Acylation / 16.1: Reduction / 17.1: Hydrolysis / 18.1: Etherification;

DOI:10.1021/jo990989b

Reference yield:

(2R,3S,4aR,6S,7R,9aS)-3-(tert-Butyl-diphenyl-silanyloxy)-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-(2-hydroxy-ethyl)-octahydro-1,5-dioxa-benzocyclohepten-7-ol (208454-47-1) → C40H56O9Si (208454-74-4)

Guidance literature:

Multi-step reaction with 18 steps

2.1: sec-butyllithium / tetrahydrofuran / -78 °C

2.2: 32 percent / tetrahydrofuran / -78 °C

3.1: 29 percent / TiCl₄; triphenylphosphine / CH₂Cl₂ / -78 - 0 °C

4.1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

5.1: N-methylmorpholine N-oxide; OsO₄ / H₂O; 2-methyl-propan-2-ol; various solvent(s) / 20 °C

6.1: lead tetraacetate / benzene / 0.5 h / 20 °C

7.1: 2.778 g / tetrahydrofuran; diethyl ether / -78 - 0 °C

8.1: 94 percent / oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / -78 - 20 °C

9.1: lithium diisopropylamide / tetrahydrofuran; hexane / 0.33 h / -78 °C

9.2: tetrahydrofuran; hexane / 0.33 h / -78 °C

10.1: N-bromosuccinimide / tetrahydrofuran / 0.75 h / 0 °C

11.1: 101.0 mg / camphorsulfonic acid / CH₂Cl₂; methanol / 0 - 20 °C

12.1: triethylamine; sulfur trioxide-pyridine complex / CH₂Cl₂; dimethylsulfoxide / 0.67 h / 0 °C

13.1: SmI₂ / tetrahydrofuran / 0.75 h / -78 °C

13.2: 4-(dimethylamino)pyridine / tetrahydrofuran / 0.5 h / 0 °C

14.1: 389.8 mg / sodium borohydride / CH₂Cl₂; methanol / 0.17 h / 0 °C

15.1: 300 mg / 4-(dimethylamino)pyridine / acetonitrile / 23 h / 20 °C

16.1: 26 percent / Bu₃SnH; azobis(isobutyronitrile) / toluene / 80 °C

17.1: tetra-n-butylammonium fluoride / tetrahydrofuran / 20 °C

18.1: 236 mg / imidazole / dimethylformamide / 0.5 h / 0 °C

With 1H-imidazole; 2,6-dimethylpyridine; lead(IV) acetate; dmap; sodium tetrahydroborate; N-Bromosuccinimide; osmium(VIII) oxide; samarium diiodide; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; sec.-butyllithium; tri-n-butyl-tin hydride; sulfur trioxide pyridine complex; titanium tetrachloride; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; triphenylphosphine; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol; benzene; 2.1: Metallation / 2.2: allylsilylation / 3.1: Cyclization / 4.1: Etherification / 5.1: Oxidation / 6.1: Oxidation / 7.1: Addition / 8.1: Oxidation / 9.1: Metallation / 9.2: Etherification / 10.1: Bromination / 11.1: Hydrolysis / 12.1: Oxidation / 13.1: Cyclization / 13.2: Acetylation / 14.1: Reduction / 15.1: Acylation / 16.1: Reduction / 17.1: Hydrolysis / 18.1: Etherification;

DOI:10.1021/jo990989b

upstream raw materials:

tert-butylchlorodiphenylsilane

((2R,3S)-3-Allyloxy-tetrahydro-pyran-2-yl)-acetaldehyde

(2R,3S,4aR,6S,7R,9aS)-3-(tert-Butyl-diphenyl-silanyloxy)-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-(2-hydroxy-ethyl)-octahydro-1,5-dioxa-benzocyclohepten-7-ol

(2R,3S,4aR,5aS,9R,10aR,12aS)-9-((2R,3S)-3-Allyloxy-tetrahydro-pyran-2-ylmethyl)-3-(tert-butyl-diphenyl-silanyloxy)-2-(tert-butyl-diphenyl-silanyloxymethyl)-decahydro-1,5,8,10-tetraoxa-benzo[b]heptalene

Downstream raw materials:

C₄₀H₅₄O₉Si

C₄₄H₆₄O₈S₂Si

C₆₈H₁₀₂O₁₄S₂Si

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