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

Base Information

• Chemical Name: (4R,5R,7S,8S)-1-bromo-9-(tert-butyldiphenylsilyloxy)-4,5,7,8-diepoxynonane
• CAS No.: 197219-44-6
• Molecular Formula: C₂₅H₃₃BrO₃Si
• Molecular Weight: 489.525
• Mol file: 197219-44-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 13 articles about (4R,5R,7S,8S)-1-bromo-9-(tert-butyldiphenylsilyloxy)-4,5,7,8-diepoxynonane 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:

pent-1-yn-5-ol (5390-04-5) → (4R,5R,7S,8S)-1-bromo-9-(tert-butyldiphenylsilyloxy)-4,5,7,8-diepoxynonane (197219-44-6)

Guidance literature:

Multi-step reaction with 12 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

12.1: disodium hydrogen phosphate; m-chloroperbenzoic acid / CH₂Cl₂ / 1 h / 0 - 25 °C

With 1H-imidazole; methanol; tert.-butylhydroperoxide; disodium hydrogenphosphate; lithium aluminium tetrahydride; n-butyllithium; carbon tetrabromide; sodium hydride; toluene-4-sulfonic acid; (+)-Weinsaeure-diethylester; 3-chloro-benzenecarboperoxoic acid; 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 / 12.1: Epoxidation;

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

Reference yield:

1-methoxy-4-pent-4-ynyloxymethyl-benzene (197219-01-5) → (4R,5R,7S,8S)-1-bromo-9-(tert-butyldiphenylsilyloxy)-4,5,7,8-diepoxynonane (197219-44-6)

Guidance literature:

Multi-step reaction with 11 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

11.1: disodium hydrogen phosphate; m-chloroperbenzoic acid / CH₂Cl₂ / 1 h / 0 - 25 °C

With 1H-imidazole; methanol; tert.-butylhydroperoxide; disodium hydrogenphosphate; lithium aluminium tetrahydride; n-butyllithium; carbon tetrabromide; toluene-4-sulfonic acid; (+)-Weinsaeure-diethylester; 3-chloro-benzenecarboperoxoic acid; 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 / 11.1: Epoxidation;

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

Reference yield:

(2E)-1-bromo-6-(4-methoxybenzyloxy)-2-hexene (197219-36-6) → (4R,5R,7S,8S)-1-bromo-9-(tert-butyldiphenylsilyloxy)-4,5,7,8-diepoxynonane (197219-44-6)

Guidance literature:

Multi-step reaction with 8 steps

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

1.2: 54 percent / tetrahydrofuran; hexane / 7 h / -78 - 25 °C

2.1: 100 percent / MeOH; p-toluenesulfonic acid monohydrate / 0.5 h / 25 °C

3.1: 94 percent / LiAlH₄ / tetrahydrofuran / 13 h / 0 - 25 °C

4.1: 94 percent / (+)-diethyl tartrate; MS₄A; tert-butyl hydroperoxide / Ti(OiPr)4 / CH₂Cl₂; toluene / 15 h / -25 °C

5.1: 100 percent / imidazole / dimethylformamide / 14 h / 0 - 25 °C

6.1: 100 percent / dichlorodicyanobenzoquinone / CH₂Cl₂; H₂O / 1.5 h / 0 - 25 °C

7.1: 81 percent / triphenylphosphine; carbon tetrabromide / CH₂Cl₂ / 0.08 h / 25 °C

8.1: disodium hydrogen phosphate; m-chloroperbenzoic acid / CH₂Cl₂ / 1 h / 0 - 25 °C

With 1H-imidazole; methanol; tert.-butylhydroperoxide; disodium hydrogenphosphate; lithium aluminium tetrahydride; n-butyllithium; carbon tetrabromide; toluene-4-sulfonic acid; (+)-Weinsaeure-diethylester; 3-chloro-benzenecarboperoxoic acid; 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: Alkylation / 2.1: methanolysis / 3.1: Reduction / 4.1: Sharpless epoxidation / 5.1: silylation / 6.1: Oxidation / 7.1: Bromination / 8.1: Epoxidation;

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

upstream raw materials:

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

pent-1-yn-5-ol

tert-butylchlorodiphenylsilane

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

Downstream raw materials:

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