(R,2E,6E)-1-acetoxy-10-(tert-butyldiphenylsilyloxy)-3,7,8-trimethyldeca-2,6-diene

Base Information

Chemical Name:(R,2E,6E)-1-acetoxy-10-(tert-butyldiphenylsilyloxy)-3,7,8-trimethyldeca-2,6-diene
CAS No.:270258-36-1
Molecular Formula:C₃₁H₄₄O₃Si
Molecular Weight:492.774
Hs Code.:

Synonyms:(R,2E,6E)-1-acetoxy-10-(tert-butyldiphenylsilyloxy)-3,7,8-trimethyldeca-2,6-diene

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Chemical Property of (R,2E,6E)-1-acetoxy-10-(tert-butyldiphenylsilyloxy)-3,7,8-trimethyldeca-2,6-diene

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Technology Process of (R,2E,6E)-1-acetoxy-10-(tert-butyldiphenylsilyloxy)-3,7,8-trimethyldeca-2,6-diene

There total 17 articles about (R,2E,6E)-1-acetoxy-10-(tert-butyldiphenylsilyloxy)-3,7,8-trimethyldeca-2,6-diene 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: 98.0%

: 108-24-7
acetic anhydride

: 270258-35-0
(R,2E,6E)-10-(tert-butyldiphenylsilyloxy)-3,7,8-trimethyldeca-2,6-dien-1-ol

: 270258-36-1
(R,2E,6E)-1-acetoxy-10-(tert-butyldiphenylsilyloxy)-3,7,8-trimethyldeca-2,6-diene

Guidance literature:: In pyridine; at 20 ℃; for 20h;
DOI:10.1002/(sici)1099-0690(200003)2000:6<955::aid-ejoc955>3.0.co;2-y

Reference yield:

: 270258-30-5
(R,E)-6-(tert-butyldiphenylsilyloxy)-3,4-dimethyl-2-hexen-1-ol

: 270258-36-1
(R,2E,6E)-1-acetoxy-10-(tert-butyldiphenylsilyloxy)-3,7,8-trimethyldeca-2,6-diene

Guidance literature:: Multi-step reaction with 6 steps

1.1: CCl₄; PPh₃ / 6 h / Heating

2.1: dimethylformamide / 15 h / 20 °C

3.1: n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 0.5 h / -50 °C

3.2: 88 percent / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 18 h / 4 °C

4.1: 85 percent / AcOH / tetrahydrofuran; H₂O / 24 h / 20 °C

5.1: 82 percent / lithium triethylhydroborate / palladium chloride-1,3-bis(diphenylphosphano)propane complex / tetrahydrofuran / 6 h / 4 °C

6.1: 98 percent / pyridine / 20 h / 20 °C

With tetrachloromethane; n-butyllithium; lithium triethylborohydride; acetic acid; triphenylphosphine; bis(diphenylphosphino)propanepalladium(II) dichloride; In tetrahydrofuran; pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; water; N,N-dimethyl-formamide; 1.1: Chlorination / 2.1: Substitution / 3.1: Metallation / 3.2: Alkylation / 4.1: Hydrolysis / 5.1: Reduction / 6.1: Acetylation;
DOI:10.1002/(sici)1099-0690(200003)2000:6<955::aid-ejoc955>3.0.co;2-y

Reference yield:

: 270258-32-7
(R,E)-6-(tert-butyldiphenylsilyloxy)-3,4-dimethyl-1-phenylsulfonyl-2-hexene

: 270258-36-1
(R,2E,6E)-1-acetoxy-10-(tert-butyldiphenylsilyloxy)-3,7,8-trimethyldeca-2,6-diene

Guidance literature:: Multi-step reaction with 4 steps

1.1: n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 0.5 h / -50 °C

1.2: 88 percent / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 18 h / 4 °C

2.1: 85 percent / AcOH / tetrahydrofuran; H₂O / 24 h / 20 °C

3.1: 82 percent / lithium triethylhydroborate / palladium chloride-1,3-bis(diphenylphosphano)propane complex / tetrahydrofuran / 6 h / 4 °C

4.1: 98 percent / pyridine / 20 h / 20 °C

With n-butyllithium; lithium triethylborohydride; acetic acid; bis(diphenylphosphino)propanepalladium(II) dichloride; In tetrahydrofuran; pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; water; 1.1: Metallation / 1.2: Alkylation / 2.1: Hydrolysis / 3.1: Reduction / 4.1: Acetylation;
DOI:10.1002/(sici)1099-0690(200003)2000:6<955::aid-ejoc955>3.0.co;2-y