(S,E)-7-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-methylhepta-1,5-dien-4-yl-3-((tert-butyldiphenylsilyl)oxy)propanoate

Base Information

• Chemical Name: (S,E)-7-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-methylhepta-1,5-dien-4-yl-3-((tert-butyldiphenylsilyl)oxy)propanoate
• CAS No.: 1437313-02-4
• Molecular Formula: C₃₂H₄₄O₅Si
• Molecular Weight: 536.784

Synonyms:(S,E)-7-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-methylhepta-1,5-dien-4-yl-3-((tert-butyldiphenylsilyl)oxy)propanoate

Chemical Property of (S,E)-7-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-methylhepta-1,5-dien-4-yl-3-((tert-butyldiphenylsilyl)oxy)propanoate

Chemical Property:

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Technology Process of (S,E)-7-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-methylhepta-1,5-dien-4-yl-3-((tert-butyldiphenylsilyl)oxy)propanoate

There total 10 articles about (S,E)-7-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-methylhepta-1,5-dien-4-yl-3-((tert-butyldiphenylsilyl)oxy)propanoate 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: 94.0%

(S,E)-7-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-methylhepta-1,5-dien-4-ol (1437312-75-8) + methyl 3-(tert-butyldiphenylsilyloxy)propanoic acid (310409-17-7) → (S,E)-7-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-methylhepta-1,5-dien-4-yl-3-((tert-butyldiphenylsilyl)oxy)propanoate (1437313-02-4)

Guidance literature:

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 0 - 20 ℃; for 17h; Inert atmosphere;

DOI:10.1002/chem.201202553

Reference yield:

(S)-5,6-di-O-isopropylidene-5,6-dihydroxy-2-hexyn-1-ol (123151-86-0) → (S,E)-7-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-methylhepta-1,5-dien-4-yl-3-((tert-butyldiphenylsilyl)oxy)propanoate (1437313-02-4)

Guidance literature:

Multi-step reaction with 7 steps

1.1: sodium bis(2-methoxyethoxy)aluminium dihydride / tetrahydrofuran; toluene / 0.83 h / 0 - 20 °C / Inert atmosphere

1.2: -78 - 20 °C

2.1: triethylamine / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere

3.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / tetrahydrofuran / 24 h / 80 °C / Inert atmosphere

4.1: potassium carbonate / methanol / 1.5 h / 20 °C

5.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

6.1: Duthaler-Hafner reagent / tetrahydrofuran; diethyl ether / 1.25 h / 0 °C / Inert atmosphere

6.2: 0.25 h / -71 °C / Inert atmosphere

6.3: 14 h / 20 °C / Inert atmosphere

7.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 17 h / 0 - 20 °C / Inert atmosphere

With dmap; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; oxalyl dichloride; Duthaler-Hafner reagent; potassium carbonate; dimethyl sulfoxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene; 5.1: |Swern Oxidation;

DOI:10.1002/chem.201202553

Reference yield:

(S, Z)-4-(2,2-dimethyl-1,3-dioxolan-4-yl)-3-iodobut-2-en-1-ol (1437312-97-4) → (S,E)-7-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-methylhepta-1,5-dien-4-yl-3-((tert-butyldiphenylsilyl)oxy)propanoate (1437313-02-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: triethylamine / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere

2.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / tetrahydrofuran / 24 h / 80 °C / Inert atmosphere

3.1: potassium carbonate / methanol / 1.5 h / 20 °C

4.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

5.1: Duthaler-Hafner reagent / tetrahydrofuran; diethyl ether / 1.25 h / 0 °C / Inert atmosphere

5.2: 0.25 h / -71 °C / Inert atmosphere

5.3: 14 h / 20 °C / Inert atmosphere

6.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 17 h / 0 - 20 °C / Inert atmosphere

With dmap; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; oxalyl dichloride; Duthaler-Hafner reagent; potassium carbonate; dimethyl sulfoxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 4.1: |Swern Oxidation;

DOI:10.1002/chem.201202553

upstream raw materials:

(S)-4-(3,3-dibromoallyl)-2,2-dimethyl-1,3-dioxolane

(S)-5,6-di-O-isopropylidene-5,6-dihydroxy-2-hexyn-1-ol

(S, Z)-4-(2,2-dimethyl-1,3-dioxolan-4-yl)-3-iodobut-2-en-1-ol

(S,E)-4-(2,2-dimethyl-1,3-dioxolan-4-yl)-3-methylbut-2-en-1-ol

Downstream raw materials:

3-((tert-butyldiphenylsilyl)oxy)-1-(((S,E)-7-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-methylhepta-1,5-dien-4-yl)oxy)propyl acetate

3-((tert-butyldiphenylsilyl)oxy)-1-(((S,E)-7-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-methylhepta-1,5-dien-4-yl)oxy)propyl acetate

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