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

Base Information

• Chemical Name: [(3Z,5E,7E,11Z)-(2R,9R)-2,9-Bis-(tert-butyl-diphenyl-silanyloxy)-heptadeca-3,5,7,11-tetraenylsulfanyl]-acetic acid methyl ester
• CAS No.: 111670-32-7
• Molecular Formula: C₅₂H₆₈O₄SSi₂
• Molecular Weight: 845.347

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 36 articles about [(3Z,5E,7E,11Z)-(2R,9R)-2,9-Bis-(tert-butyl-diphenyl-silanyloxy)-heptadeca-3,5,7,11-tetraenylsulfanyl]-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:

2-deoxy-D-ribose (22900-10-3,35536-75-5,36792-85-5,113890-34-9,113890-37-2,133813-23-7) → [(3Z,5E,7E,11Z)-(2R,9R)-2,9-Bis-(tert-butyl-diphenyl-silanyloxy)-heptadeca-3,5,7,11-tetraenylsulfanyl]-acetic acid methyl ester (111670-32-7,111670-33-8)

Guidance literature:

Multi-step reaction with 17 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.

16: acetonitrile / Ambient temperature

17: LiHMDS / tetrahydrofuran / -78 - 0 °C

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 hexamethyldisilazane; lithium diisopropyl amide; diethylazodicarboxylate; dmap; In tetrahydrofuran; pyridine; dichloromethane; toluene; acetonitrile; butanone;

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,7E,11Z)-(2R,9R)-2,9-Bis-(tert-butyl-diphenyl-silanyloxy)-heptadeca-3,5,7,11-tetraenylsulfanyl]-acetic acid methyl ester (111670-32-7)

Guidance literature:

Multi-step reaction with 17 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.

16: acetonitrile / Ambient temperature

17: LiHMDS / tetrahydrofuran / -78 - 0 °C

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 hexamethyldisilazane; lithium diisopropyl amide; diethylazodicarboxylate; dmap; In tetrahydrofuran; pyridine; dichloromethane; toluene; acetonitrile; 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,7E,11Z)-(2R,9R)-2,9-Bis-(tert-butyl-diphenyl-silanyloxy)-heptadeca-3,5,7,11-tetraenylsulfanyl]-acetic acid methyl ester (111670-32-7)

Guidance literature:

Multi-step reaction with 16 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.

15: acetonitrile / Ambient temperature

16: LiHMDS / tetrahydrofuran / -78 - 0 °C

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 hexamethyldisilazane; lithium diisopropyl amide; diethylazodicarboxylate; dmap; In tetrahydrofuran; pyridine; dichloromethane; toluene; acetonitrile; butanone;

DOI:10.1139/v87-244

upstream raw materials:

2(R)-<(tert-butyldiphenylsilyl)oxy>dec-4(Z)-enal

[(2E,4Z)-(R)-6-(tert-Butyl-diphenyl-silanyloxy)-7-methoxycarbonylmethylsulfanyl-hepta-2,4-dienyl]-triphenyl-phosphonium; bromide

2-deoxy-D-ribose

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

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