(7S,8S,4E)-1-bromo-9-(tert-butyldiphenylsilyloxy)-7,8-epoxy-4-nonene

Base Information

• Chemical Name: (7S,8S,4E)-1-bromo-9-(tert-butyldiphenylsilyloxy)-7,8-epoxy-4-nonene
• CAS No.: 197219-43-5
• Molecular Formula: C₂₅H₃₃BrO₂Si
• Molecular Weight: 473.525
• Mol file: 197219-43-5.mol

Synonyms:(7S,8S,4E)-1-bromo-9-(tert-butyldiphenylsilyloxy)-7,8-epoxy-4-nonene

Chemical Property of (7S,8S,4E)-1-bromo-9-(tert-butyldiphenylsilyloxy)-7,8-epoxy-4-nonene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (7S,8S,4E)-1-bromo-9-(tert-butyldiphenylsilyloxy)-7,8-epoxy-4-nonene

There total 12 articles about (7S,8S,4E)-1-bromo-9-(tert-butyldiphenylsilyloxy)-7,8-epoxy-4-nonene 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: 81.0%

(7S,8S,4E)-9-(tert-butyldiphenylsilyloxy)-7,8-epoxy-4-nonen-1-ol → (7S,8S,4E)-1-bromo-9-(tert-butyldiphenylsilyloxy)-7,8-epoxy-4-nonene (197219-43-5)

Guidance literature:

With carbon tetrabromide; triphenylphosphine; In dichloromethane; at 25 ℃; for 0.0833333h;

DOI:10.1016/S0040-4020(97)00780-1

Reference yield:

pent-1-yn-5-ol (5390-04-5) → (7S,8S,4E)-1-bromo-9-(tert-butyldiphenylsilyloxy)-7,8-epoxy-4-nonene (197219-43-5)

Guidance literature:

Multi-step reaction with 11 steps

1.1: NaH / tetrahydrofuran / 1 h / 0 °C

1.2: 95 percent / tetrabutylammonium iodide / tetrahydrofuran / 14 h / 25 °C

2.1: BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

2.2: 100 percent / tetrahydrofuran; hexane / 2 h / -78 - 25 °C

3.1: 100 percent / LiAlH₄ / tetrahydrofuran / 17 h / 0 - 25 °C

4.1: 90 percent / Ph₃P; CBr₄ / CH₂Cl₂ / 0.08 h / 0 - 25 °C

5.1: BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

5.2: 54 percent / tetrahydrofuran; hexane / 7 h / -78 - 25 °C

6.1: 100 percent / MeOH; p-toluenesulfonic acid monohydrate / 0.5 h / 25 °C

7.1: 94 percent / LiAlH₄ / tetrahydrofuran / 13 h / 0 - 25 °C

8.1: 94 percent / (+)-diethyl tartrate; MS₄A; tert-butyl hydroperoxide / Ti(OiPr)4 / CH₂Cl₂; toluene / 15 h / -25 °C

9.1: 100 percent / imidazole / dimethylformamide / 14 h / 0 - 25 °C

10.1: 100 percent / dichlorodicyanobenzoquinone / CH₂Cl₂; H₂O / 1.5 h / 0 - 25 °C

11.1: 81 percent / triphenylphosphine; carbon tetrabromide / CH₂Cl₂ / 0.08 h / 25 °C

With 1H-imidazole; methanol; tert.-butylhydroperoxide; lithium aluminium tetrahydride; n-butyllithium; carbon tetrabromide; sodium hydride; toluene-4-sulfonic acid; (+)-Weinsaeure-diethylester; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; titanium(IV) isopropylate; In tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; 1.1: Metallation / 1.2: Etherification / 2.1: Metallation / 2.2: Addition / 3.1: Reduction / 4.1: Bromination / 5.1: Metallation / 5.2: Alkylation / 6.1: methanolysis / 7.1: Reduction / 8.1: Sharpless epoxidation / 9.1: silylation / 10.1: Oxidation / 11.1: Bromination;

DOI:10.1016/S0040-4020(97)00780-1

Reference yield:

1-methoxy-4-pent-4-ynyloxymethyl-benzene (197219-01-5) → (7S,8S,4E)-1-bromo-9-(tert-butyldiphenylsilyloxy)-7,8-epoxy-4-nonene (197219-43-5)

Guidance literature:

Multi-step reaction with 10 steps

1.1: BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

1.2: 100 percent / tetrahydrofuran; hexane / 2 h / -78 - 25 °C

2.1: 100 percent / LiAlH₄ / tetrahydrofuran / 17 h / 0 - 25 °C

3.1: 90 percent / Ph₃P; CBr₄ / CH₂Cl₂ / 0.08 h / 0 - 25 °C

4.1: BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

4.2: 54 percent / tetrahydrofuran; hexane / 7 h / -78 - 25 °C

5.1: 100 percent / MeOH; p-toluenesulfonic acid monohydrate / 0.5 h / 25 °C

6.1: 94 percent / LiAlH₄ / tetrahydrofuran / 13 h / 0 - 25 °C

7.1: 94 percent / (+)-diethyl tartrate; MS₄A; tert-butyl hydroperoxide / Ti(OiPr)4 / CH₂Cl₂; toluene / 15 h / -25 °C

8.1: 100 percent / imidazole / dimethylformamide / 14 h / 0 - 25 °C

9.1: 100 percent / dichlorodicyanobenzoquinone / CH₂Cl₂; H₂O / 1.5 h / 0 - 25 °C

10.1: 81 percent / triphenylphosphine; carbon tetrabromide / CH₂Cl₂ / 0.08 h / 25 °C

With 1H-imidazole; methanol; tert.-butylhydroperoxide; lithium aluminium tetrahydride; n-butyllithium; carbon tetrabromide; toluene-4-sulfonic acid; (+)-Weinsaeure-diethylester; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; titanium(IV) isopropylate; In tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; 1.1: Metallation / 1.2: Addition / 2.1: Reduction / 3.1: Bromination / 4.1: Metallation / 4.2: Alkylation / 5.1: methanolysis / 6.1: Reduction / 7.1: Sharpless epoxidation / 8.1: silylation / 9.1: Oxidation / 10.1: Bromination;

DOI:10.1016/S0040-4020(97)00780-1

upstream raw materials:

pent-1-yn-5-ol

tert-butylchlorodiphenylsilane

1-methoxy-4-pent-4-ynyloxymethyl-benzene

(2E)-1-bromo-6-(4-methoxybenzyloxy)-2-hexene

Downstream raw materials:

(4S,5S,7S,8S)-1-bromo-9-(tert-butyldiphenylsilyloxy)-4,5,7,8-diepoxynonane

(4R,5R,7S,8S)-1-bromo-9-(tert-butyldiphenylsilyloxy)-4,5,7,8-diepoxynonane

(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-(2R,3aR,7aS)-hexahydro-furo[3,2-b]pyran-2-yl-ethanol