(3Z,5S,6S,7R,8S,9R,11Z,13S,14R,15S)-14-(t-butyldimethylsilyloxy)-6,16-bis(p-methoxybenzyloxy)-9-[(2,4,6-trimethylphenyl)sulfoxymethyl]-5,7,11,13,15-pentamethyl-hexadeca-1,3,11-trien-8-ol

Base Information

Chemical Name:(3Z,5S,6S,7R,8S,9R,11Z,13S,14R,15S)-14-(t-butyldimethylsilyloxy)-6,16-bis(p-methoxybenzyloxy)-9-[(2,4,6-trimethylphenyl)sulfoxymethyl]-5,7,11,13,15-pentamethyl-hexadeca-1,3,11-trien-8-ol
CAS No.:373645-66-0
Molecular Formula:C₅₃H₈₀O₉SSi
Molecular Weight:921.364
Hs Code.:

(3Z,5S,6S,7R,8S,9R,11Z,13S,14R,15S)-14-(t-butyldimethylsilyloxy)-6,16-bis(p-methoxybenzyloxy)-9-[(2,4,6-trimethylphenyl)sulfoxymethyl]-5,7,11,13,15-pentamethyl-hexadeca-1,3,11-trien-8-ol

Synonyms:(3Z,5S,6S,7R,8S,9R,11Z,13S,14R,15S)-14-(t-butyldimethylsilyloxy)-6,16-bis(p-methoxybenzyloxy)-9-[(2,4,6-trimethylphenyl)sulfoxymethyl]-5,7,11,13,15-pentamethyl-hexadeca-1,3,11-trien-8-ol

Suppliers and Price of (3Z,5S,6S,7R,8S,9R,11Z,13S,14R,15S)-14-(t-butyldimethylsilyloxy)-6,16-bis(p-methoxybenzyloxy)-9-[(2,4,6-trimethylphenyl)sulfoxymethyl]-5,7,11,13,15-pentamethyl-hexadeca-1,3,11-trien-8-ol

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

Total 0 raw suppliers

Chemical Property of (3Z,5S,6S,7R,8S,9R,11Z,13S,14R,15S)-14-(t-butyldimethylsilyloxy)-6,16-bis(p-methoxybenzyloxy)-9-[(2,4,6-trimethylphenyl)sulfoxymethyl]-5,7,11,13,15-pentamethyl-hexadeca-1,3,11-trien-8-ol

Chemical Property:

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Technology Process of (3Z,5S,6S,7R,8S,9R,11Z,13S,14R,15S)-14-(t-butyldimethylsilyloxy)-6,16-bis(p-methoxybenzyloxy)-9-[(2,4,6-trimethylphenyl)sulfoxymethyl]-5,7,11,13,15-pentamethyl-hexadeca-1,3,11-trien-8-ol

There total 48 articles about (3Z,5S,6S,7R,8S,9R,11Z,13S,14R,15S)-14-(t-butyldimethylsilyloxy)-6,16-bis(p-methoxybenzyloxy)-9-[(2,4,6-trimethylphenyl)sulfoxymethyl]-5,7,11,13,15-pentamethyl-hexadeca-1,3,11-trien-8-ol 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: 95.0%

: 773-64-8
2-mesitylenesulphonyl chloride

: 373645-65-9
(3Z,5S,6S,7S,8R,9R,11Z,13S,14R,15S)-14-(t-butyldimethylsilyloxy)-6,16-bis(p-methoxybenzyloxy)-9-(hydroxymethyl)-5,7,11,13,15-pentamethylhexadeca-1,3,11-trien-8-ol

: 373645-66-0
(3Z,5S,6S,7R,8S,9R,11Z,13S,14R,15S)-14-(t-butyldimethylsilyloxy)-6,16-bis(p-methoxybenzyloxy)-9-[(2,4,6-trimethylphenyl)sulfoxymethyl]-5,7,11,13,15-pentamethyl-hexadeca-1,3,11-trien-8-ol

Guidance literature:: With triethylamine; In dichloromethane; at 20 ℃; for 27h;
DOI:10.1021/ja011211m

Reference yield:

: 182193-69-7
(S)-1-(p-methoxybenzyloxy)-2-methylpentan-3-one

: 373645-66-0
(3Z,5S,6S,7R,8S,9R,11Z,13S,14R,15S)-14-(t-butyldimethylsilyloxy)-6,16-bis(p-methoxybenzyloxy)-9-[(2,4,6-trimethylphenyl)sulfoxymethyl]-5,7,11,13,15-pentamethyl-hexadeca-1,3,11-trien-8-ol

Guidance literature:: Multi-step reaction with 11 steps

1.1: dicyclohexylboron chloride; triethylamine / diethyl ether / 2 h / 0 °C

1.2: diethyl ether / -78 - 0 °C

2.1: dicyclohexylboron chloride; triethylamine / diethyl ether

2.2: LiBH₄ / diethyl ether

3.1: TEMPO; bis-acetoxyiodobenzene / CH₂Cl₂ / 3 h / 20 °C

4.1: KHMDS; 18-crown-6 / tetrahydrofuran; toluene / 0.5 h / -78 °C

4.2: tetrahydrofuran; toluene / 0.67 h

5.1: 1.64 g / 2,6-lutidine / CH₂Cl₂ / 4 h / -78 °C

6.1: 90 percent / DIBAL-H / CH₂Cl₂; hexane / 1 h / -78 °C

7.1: 100 percent / I₂; PPh₃; imidazole / CH₂Cl₂ / 0.75 h

8.1: LHMDS / tetrahydrofuran / 0.25 h / -78 °C

8.2: 72 percent / tetrahydrofuran / 5 h / 0 °C

9.1: LiTMP / tetrahydrofuran / 0.17 h / -100 °C

9.2: 67 percent / tetrahydrofuran / 0.12 h / -100 °C

10.1: 94 percent / LiAlH₄ / tetrahydrofuran / 5 h / -78 - -15 °C

With 1H-imidazole; 2,6-dimethylpyridine; 2,2,6,6-tetramethyl-piperidine-N-oxyl; lithium aluminium tetrahydride; 18-crown-6 ether; [bis(acetoxy)iodo]benzene; dicyclohexylboron chloride; 2,2,6,6-tetramethylpiperidinyl-lithium; iodine; potassium hexamethylsilazane; diisobutylaluminium hydride; triethylamine; triphenylphosphine; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; toluene;
DOI:10.1021/jo048534w

Reference yield:

: 261968-12-1
1-(p-methoxybenzyloxy)-5-hydroxy-2,4,6-trimethyl-6-hepten-3-one

: 373645-66-0
(3Z,5S,6S,7R,8S,9R,11Z,13S,14R,15S)-14-(t-butyldimethylsilyloxy)-6,16-bis(p-methoxybenzyloxy)-9-[(2,4,6-trimethylphenyl)sulfoxymethyl]-5,7,11,13,15-pentamethyl-hexadeca-1,3,11-trien-8-ol

Guidance literature:: Multi-step reaction with 12 steps

1.1: 96 percent / SmI₂ / tetrahydrofuran / 1.5 h / -10 °C

2.1: 97 percent / K₂CO₃ / methanol; H₂O / 5 h / 20 °C

3.1: 94 percent / PPTS / toluene / 4 h / Heating

4.1: NaIO₄; NaHCO₃ / methanol; H₂O / 2 h / 20 °C

5.1: 82 percent / DBU; 1-(t-butyldimethylsiloxy)-1-methoxyethene / various solvent(s) / 8 h / Heating

6.1: 85 percent / methanol / 0 - 20 °C

7.1: 99 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / -78 °C

8.1: 91 percent / aq. KOH / methanol / 1 h / Heating

9.1: 86 percent / DCC; 4-DMAP / CH₂Cl₂ / 16 h / 20 °C

10.1: LiTMP; LiBr / tetrahydrofuran / -100 °C

10.2: 81 percent / tetrahydrofuran / 0.08 h / -100 °C

11.1: 88 percent / LiAlH₄ / tetrahydrofuran / -78 - -10 °C

12.1: 95 percent / Et₃N / CH₂Cl₂ / 27 h / 20 °C

With 2,6-dimethylpyridine; dmap; potassium hydroxide; sodium periodate; lithium aluminium tetrahydride; samarium diiodide; 2,2,6,6-tetramethylpiperidinyl-lithium; ketene t-butyldimethylsilyl methyl acetal; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; dicyclohexyl-carbodiimide; lithium bromide; In tetrahydrofuran; methanol; dichloromethane; water; toluene; 1.1: Evans-Tischenko reaction / 5.1: Claisen rearrangement;
DOI:10.1021/ja011211m