C₈₀H₁₅₁IO₁₂Si₅

Base Information

• Chemical Name: C₈₀H₁₅₁IO₁₂Si₅
• CAS No.: 359796-03-5
• Molecular Formula: C₈₀H₁₅₁IO₁₂Si₅
• Molecular Weight: 1572.4
• Mol file: 359796-03-5.mol

Synonyms:C₈₀H₁₅₁IO₁₂Si₅

Chemical Property of C₈₀H₁₅₁IO₁₂Si₅

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of C₈₀H₁₅₁IO₁₂Si₅

There total 20 articles about C₈₀H₁₅₁IO₁₂Si₅ 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: 85.0%

t-butyldimethylsiyl triflate (69739-34-0) + C74H137IO12Si4 (359796-02-4) → C80H151IO12Si5 (359796-03-5)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃; for 1.5h;

DOI:10.1021/jo0104429

Reference yield:

3-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-octanoic acid (359796-12-6) → C80H151IO12Si5 (359796-03-5)

Guidance literature:

Multi-step reaction with 14 steps

1: 91 mg / 4-(dimethylamino)pyridine; 1,3-dicyclohexylcarbodiimide / CH₂Cl₂ / 9 h / 20 °C

2: 67 percent / halide-free lithium diisopropylamide / tetrahydrofuran; diethyl ether / 40.5 h / -78 - -18 °C

3: 73 percent / HF / H₂O; acetonitrile / 120 h / 20 °C

4: imidazole / dimethylformamide / 17 h / 20 °C

5: 86 percent / imidazole / dimethylformamide / 7 h / 20 °C

6: 88 percent / samarium diiodide / tetrahydrofuran; propan-2-ol / 5.5 h / 20 °C

7: 90 percent / triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 3 h

8: 44 percent / hydrofluoric acid*pyridine / tetrahydrofuran; pyridine / 11 h / 20 °C

9: 96 percent / oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / 2.33 h / -78 - 20 °C

10: 99 percent / lithium hydroxide monohydrate / methanol; tetrahydrofuran; H₂O / 20 h / 20 °C

11: 96 percent / DMAP / pyridine

12: 76 percent / diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 0.75 h / -78 °C

13: 62 percent / titanium(IV) chloride; i-Pr₂NEt / CH₂Cl₂ / -78 - -30 °C

14: 85 percent / 2,6-lutidine / CH₂Cl₂ / 1.5 h / 0 °C

With 1H-imidazole; 2,6-dimethylpyridine; dmap; lithium hydroxide; n-butyllithium; samarium diiodide; oxalyl dichloride; hydrogen fluoride; titanium tetrachloride; pyridine hydrogenfluoride; dimethyl sulfoxide; triethylamine; diisopropylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; lithium diisopropyl amide; In tetrahydrofuran; pyridine; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; isopropyl alcohol; acetonitrile; 9: Swern oxidation / 12: Wadsworth-Emmons condensation;

DOI:10.1021/jo0104429

Reference yield:

(2S,3S,4S,6R,8S,9S)-3,9-dimethyl-8-[(R)-2-hydroxy-1-propyl]-2-[(R)-3-(hydroxymethyl)-1-pentyl]-1,7-dioxaspiro[5.5]undecan-4-ol (131725-13-8) → C80H151IO12Si5 (359796-03-5)

Guidance literature:

Multi-step reaction with 9 steps

1: 13 mg / 2,6-lutidine / CH₂Cl₂ / 2.5 h / -78 °C

2: 90 percent / triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 3 h

3: 44 percent / hydrofluoric acid*pyridine / tetrahydrofuran; pyridine / 11 h / 20 °C

4: 96 percent / oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / 2.33 h / -78 - 20 °C

5: 99 percent / lithium hydroxide monohydrate / methanol; tetrahydrofuran; H₂O / 20 h / 20 °C

6: 96 percent / DMAP / pyridine

7: 76 percent / diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 0.75 h / -78 °C

8: 62 percent / titanium(IV) chloride; i-Pr₂NEt / CH₂Cl₂ / -78 - -30 °C

9: 85 percent / 2,6-lutidine / CH₂Cl₂ / 1.5 h / 0 °C

With 2,6-dimethylpyridine; dmap; lithium hydroxide; n-butyllithium; oxalyl dichloride; titanium tetrachloride; pyridine hydrogenfluoride; dimethyl sulfoxide; triethylamine; diisopropylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; pyridine; methanol; hexane; dichloromethane; water; 4: Swern oxidation / 7: Wadsworth-Emmons condensation;

DOI:10.1021/jo0104429

upstream raw materials:

t-butyldimethylsiyl triflate

C₇₄H₁₃₇IO₁₂Si₄

3-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-octanoic acid

(2S,3S,4S,6R,8S,9S)-3,9-dimethyl-8-[(R)-2-hydroxy-1-propyl]-2-[(R)-3-(hydroxymethyl)-1-pentyl]-1,7-dioxaspiro[5.5]undecan-4-ol