C₇₄H₁₃₇IO₁₂Si₄

Base Information

• Chemical Name: C₇₄H₁₃₇IO₁₂Si₄
• CAS No.: 359796-02-4
• Molecular Formula: C₇₄H₁₃₇IO₁₂Si₄
• Molecular Weight: 1458.14
• Mol file: 359796-02-4.mol

Synonyms:C₇₄H₁₃₇IO₁₂Si₄

Chemical Property of C₇₄H₁₃₇IO₁₂Si₄

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of C₇₄H₁₃₇IO₁₂Si₄

There total 19 articles about C₇₄H₁₃₇IO₁₂Si₄ 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: 62.0%

(E)-(4S,5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-4,6-dimethyl-7-oxo-non-2-enoic acid (2S,3R,4S,6R,8S,9S)-8-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-propyl]-2-((E)-(R)-3-ethyl-5-iodo-pent-4-enyl)-3,9-dimethyl-1,7-dioxa-spiro[5.5]undec-4-yl ester (203063-87-0) + (2R,3R,4R,5S,6R)-5,7-bis-(tert-butyldimethylsilanyloxy)-3-(4-methoxybenzyloxy)-2,4,6-trimethylheptanal (152328-93-3) → C74H137IO12Si4 (359796-02-4)

Guidance literature:

With titanium tetrachloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at -78 - -30 ℃;

DOI:10.1021/jo0104429

Reference yield:

3-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-octanoic acid (359796-12-6) → C74H137IO12Si4 (359796-02-4)

Guidance literature:

Multi-step reaction with 13 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

With 1H-imidazole; 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,3R,4S,6R,8S,9S)-4-benzoyloxy-3,9-dimethyl-8-{(R)-2-[(tert-butyldimethylsilyl)oxy]-1-propyl}-2-[(R)-3-hydroxymethyl-1-pentyl]-1,7-dioxaspiro[5.5]undecane (131704-24-0) → C74H137IO12Si4 (359796-02-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 96 percent / oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / 2.33 h / -78 - 20 °C

2: 99 percent / lithium hydroxide monohydrate / methanol; tetrahydrofuran; H₂O / 20 h / 20 °C

3: 96 percent / DMAP / pyridine

4: 76 percent / diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 0.75 h / -78 °C

5: 62 percent / titanium(IV) chloride; i-Pr₂NEt / CH₂Cl₂ / -78 - -30 °C

With dmap; lithium hydroxide; n-butyllithium; oxalyl dichloride; titanium tetrachloride; dimethyl sulfoxide; triethylamine; diisopropylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; pyridine; methanol; hexane; dichloromethane; water; 1: Swern oxidation / 4: Wadsworth-Emmons condensation;

DOI:10.1021/jo0104429

upstream raw materials:

(E)-(4S,5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-4,6-dimethyl-7-oxo-non-2-enoic acid (2S,3R,4S,6R,8S,9S)-8-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-propyl]-2-((E)-(R)-3-ethyl-5-iodo-pent-4-enyl)-3,9-dimethyl-1,7-dioxa-spiro[5.5]undec-4-yl ester

(2R,3R,4R,5S,6R)-5,7-bis-(tert-butyldimethylsilanyloxy)-3-(4-methoxybenzyloxy)-2,4,6-trimethylheptanal

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

Downstream raw materials:

C₇₁H₁₁₉IO₁₄SSi₂

C₆₂H₁₀₉IO₁₂Si₂

C₈₀H₁₅₁IO₁₂Si₅