(E)-(R)-6-(tert-Butyl-diphenyl-silanyloxy)-4-methyl-hex-2-enoic acid methyl ester

Base Information

• Chemical Name: (E)-(R)-6-(tert-Butyl-diphenyl-silanyloxy)-4-methyl-hex-2-enoic acid methyl ester
• CAS No.: 173339-02-1
• Molecular Formula: C₂₄H₃₂O₃Si
• Molecular Weight: 396.602

Synonyms:(E)-(R)-6-(tert-Butyl-diphenyl-silanyloxy)-4-methyl-hex-2-enoic acid methyl ester

Chemical Property of (E)-(R)-6-(tert-Butyl-diphenyl-silanyloxy)-4-methyl-hex-2-enoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Useful:

Technology Process of (E)-(R)-6-(tert-Butyl-diphenyl-silanyloxy)-4-methyl-hex-2-enoic acid methyl ester

There total 9 articles about (E)-(R)-6-(tert-Butyl-diphenyl-silanyloxy)-4-methyl-hex-2-enoic acid methyl ester 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: 79.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + (E)-(R)-6-(tert-Butyl-diphenyl-silanyloxy)-4-methyl-hex-2-enal (281661-33-4) → (E)-(R)-6-(tert-Butyl-diphenyl-silanyloxy)-4-methyl-hex-2-enoic acid methyl ester (173339-02-1)

Guidance literature:

(E)-(R)-6-(tert-Butyl-diphenyl-silanyloxy)-4-methyl-hex-2-enal; With sodium chlorite; sodium dihydrogenphosphate; dihydrogen peroxide; In water; acetonitrile; at 20 ℃; for 21h;

diazomethane; In diethyl ether; Further stages.;

DOI:10.1021/jo9918450

Reference yield:

(S)-3,7-dimethyl-6-octen-1-ol (7540-51-4) → (E)-(R)-6-(tert-Butyl-diphenyl-silanyloxy)-4-methyl-hex-2-enoic acid methyl ester (173339-02-1)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 99 percent / Et₃N; DMAP / 1,2-dichloro-ethane / 8 h / 20 °C

2.1: O₃; NaHCO₃ / methanol; CHCl₃ / -15 °C

2.2: Me₂S / CHCl₃; methanol / 10 h / -15 - 20 °C

3.1: aq. NaClO₂; 2-methyl-2-butene; NaH₂PO₄ / 2-methyl-propan-2-ol / 2 h / 20 °C

4.1: 16.7 g / DBU / acetonitrile / 8 h / 20 °C

5.1: LDA / tetrahydrofuran; hexane / 1 h

5.2: hexane; tetrahydrofuran / 0.5 h / 20 °C

6.1: mCPBA; Na₂HPO₄ / CHCl₃ / -40 - 20 °C

7.1: 78.0 g / toluene / 2 h / Heating

With dmap; sodium chlorite; disodium hydrogenphosphate; sodium dihydrogenphosphate; 2-methyl-but-2-ene; sodium hydrogencarbonate; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; In tetrahydrofuran; methanol; hexane; chloroform; 1,2-dichloro-ethane; toluene; acetonitrile; tert-butyl alcohol;

DOI:10.1248/cpb.51.640

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → (E)-(R)-6-(tert-Butyl-diphenyl-silanyloxy)-4-methyl-hex-2-enoic acid methyl ester (173339-02-1)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 99 percent / Et₃N; DMAP / 1,2-dichloro-ethane / 8 h / 20 °C

2.1: O₃; NaHCO₃ / methanol; CHCl₃ / -15 °C

2.2: Me₂S / CHCl₃; methanol / 10 h / -15 - 20 °C

3.1: aq. NaClO₂; 2-methyl-2-butene; NaH₂PO₄ / 2-methyl-propan-2-ol / 2 h / 20 °C

4.1: 16.7 g / DBU / acetonitrile / 8 h / 20 °C

5.1: LDA / tetrahydrofuran; hexane / 1 h

5.2: hexane; tetrahydrofuran / 0.5 h / 20 °C

6.1: mCPBA; Na₂HPO₄ / CHCl₃ / -40 - 20 °C

7.1: 78.0 g / toluene / 2 h / Heating

With dmap; sodium chlorite; disodium hydrogenphosphate; sodium dihydrogenphosphate; 2-methyl-but-2-ene; sodium hydrogencarbonate; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; In tetrahydrofuran; methanol; hexane; chloroform; 1,2-dichloro-ethane; toluene; acetonitrile; tert-butyl alcohol;

DOI:10.1248/cpb.51.640

upstream raw materials:

diazomethane

(E)-(R)-6-(tert-Butyl-diphenyl-silanyloxy)-4-methyl-hex-2-enal

(S)-3,7-dimethyl-6-octen-1-ol

tert-butylchlorodiphenylsilane

Downstream raw materials:

3-[3-(tert-butyl-diphenyl-silanyloxy)-1-methyl-propyl]-pent-4-enoic acid methyl ester

3-[3-(tert-butyl-diphenyl-silanyloxy)-1-methyl-propyl]-pent-4-enoic acid methyl ester

{2-[(R)-4-(tert-butyldiphenylsiloxy)butyl]-(1R,2S)-cyclopropyl}methanol

3-[3-(tert-butyl-diphenyl-silanyloxy)-1-methyl-propyl]-pent-4-en-1-ol

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