(3Z,11Z)-(5S,6S,7R,9S,13S,14S,15S)-14-(tert-Butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-5,7,9,11,13,15-hexamethyl-heptadeca-1,3,11,16-tetraen-8-one

Base Information

• Chemical Name: (3Z,11Z)-(5S,6S,7R,9S,13S,14S,15S)-14-(tert-Butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-5,7,9,11,13,15-hexamethyl-heptadeca-1,3,11,16-tetraen-8-one
• CAS No.: 184291-48-3
• Molecular Formula: C₃₇H₆₀O₄Si
• Molecular Weight: 596.966

Synonyms:(3Z,11Z)-(5S,6S,7R,9S,13S,14S,15S)-14-(tert-Butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-5,7,9,11,13,15-hexamethyl-heptadeca-1,3,11,16-tetraen-8-one

Chemical Property of (3Z,11Z)-(5S,6S,7R,9S,13S,14S,15S)-14-(tert-Butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-5,7,9,11,13,15-hexamethyl-heptadeca-1,3,11,16-tetraen-8-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3Z,11Z)-(5S,6S,7R,9S,13S,14S,15S)-14-(tert-Butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-5,7,9,11,13,15-hexamethyl-heptadeca-1,3,11,16-tetraen-8-one

There total 31 articles about (3Z,11Z)-(5S,6S,7R,9S,13S,14S,15S)-14-(tert-Butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-5,7,9,11,13,15-hexamethyl-heptadeca-1,3,11,16-tetraen-8-one 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:

t-butyldimethylsiyl triflate (69739-34-0) → (3Z,11Z)-(5S,6S,7R,9S,13S,14S,15S)-14-(tert-Butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-5,7,9,11,13,15-hexamethyl-heptadeca-1,3,11,16-tetraen-8-one (184291-48-3)

Guidance literature:

Multi-step reaction with 14 steps

1: 93 percent / Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

2: 1.) O₃, pyridine, 2.) Me₂S / 1.) CH₃OH, CH₂Cl₂, -78 deg C, 2.) CH₃OH, CH₂Cl₂, RT, 12 h

3: 1.) KHMDS, 18-crown-6 / 1.) THF, toluene, -78 deg C, 10 min, 2.) THF, toluene, 0 deg C, 5 h

4: 92 percent / LiAlH₄ / tetrahydrofuran / 0.5 h / 0 °C

5: 96 percent / pyridine / CH₂Cl₂ / 4 h / Ambient temperature

6: 90 percent / HF, pyridine / tetrahydrofuran / 9 h / Ambient temperature

7: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 45 min, 2.) CH₂Cl₂, from -78 to RT, 20 min

8: 1.) KOtBu / 1.) THF, -78 deg C, 10 min, 2.) THF, -50 deg C, 21 h

9: 88 percent / H₂ / 10percent Pd*BaSO₄ / methanol; quinoline / 0.17 h

10: DIBAL-H

11: Et₃N

12: LiBr

13: LDA

14: 1.) LiN(SiMe₂Ph)2 / 1.) THF, -78 deg C, 1 h, 2.) THF, RT, 3 h

With pyridine; lithium aluminium tetrahydride; oxalyl dichloride; 18-crown-6 ether; dimethylsulfide; lithium bis(dimethylphenylsilyl)amide; hydrogen fluoride; potassium tert-butylate; hydrogen; potassium hexamethylsilazane; diisobutylaluminium hydride; ozone; dimethyl sulfoxide; triethylamine; lithium bromide; lithium diisopropyl amide; palladium on barium sulfate; In tetrahydrofuran; quinoline; methanol; dichloromethane;

DOI:10.1021/ja961374o

Reference yield:

(2S,3R,4S)-1-(tert-butyldimethylsilyloxy)-2,4-dimethylhex-5-en-3-ol (106296-58-6,106357-21-5,106357-23-7,106357-22-6) → (3Z,11Z)-(5S,6S,7R,9S,13S,14S,15S)-14-(tert-Butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-5,7,9,11,13,15-hexamethyl-heptadeca-1,3,11,16-tetraen-8-one (184291-48-3)

Guidance literature:

Multi-step reaction with 14 steps

1: 93 percent / Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

2: 1.) O₃, pyridine, 2.) Me₂S / 1.) CH₃OH, CH₂Cl₂, -78 deg C, 2.) CH₃OH, CH₂Cl₂, RT, 12 h

3: 1.) KHMDS, 18-crown-6 / 1.) THF, toluene, -78 deg C, 10 min, 2.) THF, toluene, 0 deg C, 5 h

4: 92 percent / LiAlH₄ / tetrahydrofuran / 0.5 h / 0 °C

5: 96 percent / pyridine / CH₂Cl₂ / 4 h / Ambient temperature

6: 90 percent / HF, pyridine / tetrahydrofuran / 9 h / Ambient temperature

7: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 45 min, 2.) CH₂Cl₂, from -78 to RT, 20 min

8: 1.) KOtBu / 1.) THF, -78 deg C, 10 min, 2.) THF, -50 deg C, 21 h

9: 88 percent / H₂ / 10percent Pd*BaSO₄ / methanol; quinoline / 0.17 h

10: DIBAL-H

11: Et₃N

12: LiBr

13: LDA

14: 1.) LiN(SiMe₂Ph)2 / 1.) THF, -78 deg C, 1 h, 2.) THF, RT, 3 h

With pyridine; lithium aluminium tetrahydride; oxalyl dichloride; 18-crown-6 ether; dimethylsulfide; lithium bis(dimethylphenylsilyl)amide; hydrogen fluoride; potassium tert-butylate; hydrogen; potassium hexamethylsilazane; diisobutylaluminium hydride; ozone; dimethyl sulfoxide; triethylamine; lithium bromide; lithium diisopropyl amide; palladium on barium sulfate; In tetrahydrofuran; quinoline; methanol; dichloromethane;

DOI:10.1021/ja961374o

Reference yield:

4R,6-bis(tert-butyldimethylsilanyloxy)-3S,5S-dimethylhex-1-ene (457623-10-8) → (3Z,11Z)-(5S,6S,7R,9S,13S,14S,15S)-14-(tert-Butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-5,7,9,11,13,15-hexamethyl-heptadeca-1,3,11,16-tetraen-8-one (184291-48-3)

Guidance literature:

Multi-step reaction with 13 steps

1: 1.) O₃, pyridine, 2.) Me₂S / 1.) CH₃OH, CH₂Cl₂, -78 deg C, 2.) CH₃OH, CH₂Cl₂, RT, 12 h

2: 1.) KHMDS, 18-crown-6 / 1.) THF, toluene, -78 deg C, 10 min, 2.) THF, toluene, 0 deg C, 5 h

3: 92 percent / LiAlH₄ / tetrahydrofuran / 0.5 h / 0 °C

4: 96 percent / pyridine / CH₂Cl₂ / 4 h / Ambient temperature

5: 90 percent / HF, pyridine / tetrahydrofuran / 9 h / Ambient temperature

6: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 45 min, 2.) CH₂Cl₂, from -78 to RT, 20 min

7: 1.) KOtBu / 1.) THF, -78 deg C, 10 min, 2.) THF, -50 deg C, 21 h

8: 88 percent / H₂ / 10percent Pd*BaSO₄ / methanol; quinoline / 0.17 h

9: DIBAL-H

10: Et₃N

11: LiBr

12: LDA

13: 1.) LiN(SiMe₂Ph)2 / 1.) THF, -78 deg C, 1 h, 2.) THF, RT, 3 h

With pyridine; lithium aluminium tetrahydride; oxalyl dichloride; 18-crown-6 ether; dimethylsulfide; lithium bis(dimethylphenylsilyl)amide; hydrogen fluoride; potassium tert-butylate; hydrogen; potassium hexamethylsilazane; diisobutylaluminium hydride; ozone; dimethyl sulfoxide; triethylamine; lithium bromide; lithium diisopropyl amide; palladium on barium sulfate; In tetrahydrofuran; quinoline; methanol; dichloromethane;

DOI:10.1021/ja961374o

upstream raw materials:

methyl iodide

t-butyldimethylsiyl triflate

p-Methoxybenzyl bromide

(2S,3R,4S)-1-(tert-butyldimethylsilyloxy)-2,4-dimethylhex-5-en-3-ol

Post a RFQ

Cas No.:

Product Name:

Quantity:

Please select Metric Ton KG G Pound L ML

Email:

Company name:

Valid Period:

Detailed Requirements:

• Sample
• MOQ
• GMP
• FDA
• Price
  FOB CIF CFR EXW
• Urgent purchase

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

Remove

Submit

1

What can I do for you?
Get Best Price

Get Best Price for 184291-48-3 (3Z,11Z)-(5S,6S,7R,9S,13S,14S,15S)-14-(tert-Butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-5,7,9,11,13,15-hexamethyl-heptadeca-1,3,11,16-tetraen-8-one

Send

Send

Metric Ton KG G Pound L ML

Send

Send