C₆₈H₁₀₂O₁₄S₂Si

Base Information

• Chemical Name: C₆₈H₁₀₂O₁₄S₂Si
• CAS No.: 208454-61-9
• Molecular Formula: C₆₈H₁₀₂O₁₄S₂Si
• Molecular Weight: 1235.77

Synonyms:C₆₈H₁₀₂O₁₄S₂Si

Chemical Property of C₆₈H₁₀₂O₁₄S₂Si

Chemical Property:

Purity/Quality:

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Technology Process of C₆₈H₁₀₂O₁₄S₂Si

There total 24 articles about C₆₈H₁₀₂O₁₄S₂Si 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:

C28H44O8S2 (208454-44-8) + C58H74O7PSi(1+)*I(1-) → C68H102O14S2Si (208454-61-9)

Guidance literature:

C₅₈H₇₄O₇PSi⁽¹⁺⁾*I^(1-); With n-butyllithium; In tetrahydrofuran; hexane;

C₂₈H₄₄O₈S₂; With N,N,N,N,N,N-hexamethylphosphoric triamide; In tetrahydrofuran; hexane; at -78 - 20 ℃;

DOI:10.1021/jo990989b

Reference yield:

((2R,3S)-3-Allyloxy-tetrahydro-pyran-2-yl)-acetaldehyde (208454-48-2) → C68H102O14S2Si (208454-61-9)

Guidance literature:

Multi-step reaction with 23 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

19.1: 94 percent / oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / -78 - 20 °C

20.1: TiCl₄ / CH₂Cl₂ / 1.5 h / -78 °C

21.1: 163.4 mg / tetra-n-butylammonium fluoride / tetrahydrofuran / 20 °C

22.1: triethylamine; sulfur trioxide-pyridine complex / CH₂Cl₂; dimethylsulfoxide / 0.5 h / 0 °C

23.1: butyllithium / tetrahydrofuran; hexane

23.2: 210.6 mg / HMPA / tetrahydrofuran; hexane / -78 - 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; lead(IV) acetate; dmap; sodium tetrahydroborate; N-Bromosuccinimide; osmium(VIII) oxide; n-butyllithium; 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 / 19.1: Oxidation / 20.1: Addition / 21.1: Hydrolysis / 22.1: Oxidation / 23.1: Dehydroiodination / 23.2: Addition;

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) → C68H102O14S2Si (208454-61-9)

Guidance literature:

Multi-step reaction with 23 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

19.1: 94 percent / oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / -78 - 20 °C

20.1: TiCl₄ / CH₂Cl₂ / 1.5 h / -78 °C

21.1: 163.4 mg / tetra-n-butylammonium fluoride / tetrahydrofuran / 20 °C

22.1: triethylamine; sulfur trioxide-pyridine complex / CH₂Cl₂; dimethylsulfoxide / 0.5 h / 0 °C

23.1: butyllithium / tetrahydrofuran; hexane

23.2: 210.6 mg / HMPA / tetrahydrofuran; hexane / -78 - 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; lead(IV) acetate; dmap; sodium tetrahydroborate; N-Bromosuccinimide; osmium(VIII) oxide; n-butyllithium; 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 / 19.1: Oxidation / 20.1: Addition / 21.1: Hydrolysis / 22.1: Oxidation / 23.1: Dehydroiodination / 23.2: Addition;

DOI:10.1021/jo990989b

upstream raw materials:

C₂₈H₄₄O₈S₂

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

C₂₈H₄₆O₈S₂

(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

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