[(3Z,5E)-(R)-7-Bromo-2-(tert-butyl-diphenyl-silanyloxy)-hepta-3,5-dienylsulfanyl]-acetic acid methyl ester

Base Information

• Chemical Name: [(3Z,5E)-(R)-7-Bromo-2-(tert-butyl-diphenyl-silanyloxy)-hepta-3,5-dienylsulfanyl]-acetic acid methyl ester
• CAS No.: 111975-62-3
• Molecular Formula: C₂₆H₃₃BrO₃SSi
• Molecular Weight: 533.602

Synonyms:[(3Z,5E)-(R)-7-Bromo-2-(tert-butyl-diphenyl-silanyloxy)-hepta-3,5-dienylsulfanyl]-acetic acid methyl ester

Chemical Property of [(3Z,5E)-(R)-7-Bromo-2-(tert-butyl-diphenyl-silanyloxy)-hepta-3,5-dienylsulfanyl]-acetic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of [(3Z,5E)-(R)-7-Bromo-2-(tert-butyl-diphenyl-silanyloxy)-hepta-3,5-dienylsulfanyl]-acetic acid methyl ester

There total 15 articles about [(3Z,5E)-(R)-7-Bromo-2-(tert-butyl-diphenyl-silanyloxy)-hepta-3,5-dienylsulfanyl]-acetic 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: 82.0%

[(3Z,5E)-(R)-2-(tert-Butyl-diphenyl-silanyloxy)-7-hydroxy-hepta-3,5-dienylsulfanyl]-acetic acid methyl ester (111670-29-2) → [(3Z,5E)-(R)-7-Bromo-2-(tert-butyl-diphenyl-silanyloxy)-hepta-3,5-dienylsulfanyl]-acetic acid methyl ester (111975-62-3)

Guidance literature:

With carbon tetrabromide; temephos; In dichloromethane; 0 deg C to room temp.;

DOI:10.1139/v87-244

Reference yield:

2-deoxy-D-ribose (22900-10-3,35536-75-5,36792-85-5,113890-34-9,113890-37-2,133813-23-7) → [(3Z,5E)-(R)-7-Bromo-2-(tert-butyl-diphenyl-silanyloxy)-hepta-3,5-dienylsulfanyl]-acetic acid methyl ester (111975-62-3)

Guidance literature:

Multi-step reaction with 15 steps

2: (i-Pr)2NEt / DMAP / CH₂Cl₂

3: pyridine; CH₂Cl₂

4: DBU / pyridine

5: 92 percent / LDA / tetrahydrofuran / 0 °C

6: 89 percent / triphenylphosphine, DEAD / tetrahydrofuran / Ambient temperature

7: 79 percent / DIBAH / toluene / -10 deg C to room temp.

8: DMAP / pyridine / 50 °C

9: tetrabutylammonium fluoride / tetrahydrofuran / Ambient temperature

10: 63 percent / triethylamine / CH₂Cl₂ / Ambient temperature

11: 87 percent / (i-Pr)2NEt / CH₂Cl₂ / Ambient temperature

12: 83 percent / NaI / butan-2-one / 70 °C

13: 96 percent / NaH / tetrahydrofuran / 4 h / 50 °C

14: 63 percent / 20 percent aq. TFA / CH₂Cl₂

15: 82 percent / CBr₄, DIPHOS / CH₂Cl₂ / 0 deg C to room temp.

With carbon tetrabromide; temephos; tetrabutyl ammonium fluoride; sodium hydride; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trifluoroacetic acid; sodium iodide; lithium diisopropyl amide; diethylazodicarboxylate; dmap; In tetrahydrofuran; pyridine; dichloromethane; toluene; butanone;

DOI:10.1139/v87-244

Reference yield:

ethyl 2-[(4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]acetate (79308-52-4) → [(3Z,5E)-(R)-7-Bromo-2-(tert-butyl-diphenyl-silanyloxy)-hepta-3,5-dienylsulfanyl]-acetic acid methyl ester (111975-62-3)

Guidance literature:

Multi-step reaction with 14 steps

1: (i-Pr)2NEt / DMAP / CH₂Cl₂

2: pyridine; CH₂Cl₂

3: DBU / pyridine

4: 92 percent / LDA / tetrahydrofuran / 0 °C

5: 89 percent / triphenylphosphine, DEAD / tetrahydrofuran / Ambient temperature

6: 79 percent / DIBAH / toluene / -10 deg C to room temp.

7: DMAP / pyridine / 50 °C

8: tetrabutylammonium fluoride / tetrahydrofuran / Ambient temperature

9: 63 percent / triethylamine / CH₂Cl₂ / Ambient temperature

10: 87 percent / (i-Pr)2NEt / CH₂Cl₂ / Ambient temperature

11: 83 percent / NaI / butan-2-one / 70 °C

12: 96 percent / NaH / tetrahydrofuran / 4 h / 50 °C

13: 63 percent / 20 percent aq. TFA / CH₂Cl₂

14: 82 percent / CBr₄, DIPHOS / CH₂Cl₂ / 0 deg C to room temp.

With carbon tetrabromide; temephos; tetrabutyl ammonium fluoride; sodium hydride; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trifluoroacetic acid; sodium iodide; lithium diisopropyl amide; diethylazodicarboxylate; dmap; In tetrahydrofuran; pyridine; dichloromethane; toluene; butanone;

DOI:10.1139/v87-244

upstream raw materials:

[(3Z,5E)-(R)-2-(tert-Butyl-diphenyl-silanyloxy)-7-hydroxy-hepta-3,5-dienylsulfanyl]-acetic acid methyl ester

2-deoxy-D-ribose

ethyl 2-[(4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]acetate

7-O-(triphenylmethyl)-3(Z),5(E)-heptadiene-1,2(S),7-triol

Downstream raw materials:

[(3Z,5E,7E,11Z)-(2R,9R)-2,9-Bis-(tert-butyl-diphenyl-silanyloxy)-17,17,17-trifluoro-heptadeca-3,5,7,11-tetraenylsulfanyl]-acetic acid methyl ester

[(3Z,5E,7E,11Z)-(2R,9R)-2,9-Bis-(tert-butyl-diphenyl-silanyloxy)-17,17,17-trifluoro-heptadeca-3,5,7,11-tetraenylsulfanyl]-acetic acid methyl ester

[(3Z,5E,7E,11Z)-(2R,9R)-2,9-Bis-(tert-butyl-diphenyl-silanyloxy)-heptadeca-3,5,7,11-tetraenylsulfanyl]-acetic acid methyl ester

[(3Z,5E,7E,11Z)-(2R,9R)-2,9-Bis-(tert-butyl-diphenyl-silanyloxy)-heptadeca-3,5,7,11-tetraenylsulfanyl]-acetic acid methyl ester

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