(3Z,5S,6S,7S,8R,9S,11Z,13S,14R,15S)-14-(t-butyldimethylsilyloxy)-6,16-bis-(p-methoxybenzyloxy)-5,7,9,11,13,15-hexamethyl-hexadeca-1,3,11-trien-8-ol

Base Information

• Chemical Name: (3Z,5S,6S,7S,8R,9S,11Z,13S,14R,15S)-14-(t-butyldimethylsilyloxy)-6,16-bis-(p-methoxybenzyloxy)-5,7,9,11,13,15-hexamethyl-hexadeca-1,3,11-trien-8-ol
• CAS No.: 261968-22-3
• Molecular Formula: C₄₄H₇₀O₆Si
• Molecular Weight: 723.122
• Mol file: 261968-22-3.mol

Synonyms:(3Z,5S,6S,7S,8R,9S,11Z,13S,14R,15S)-14-(t-butyldimethylsilyloxy)-6,16-bis-(p-methoxybenzyloxy)-5,7,9,11,13,15-hexamethyl-hexadeca-1,3,11-trien-8-ol

Chemical Property of (3Z,5S,6S,7S,8R,9S,11Z,13S,14R,15S)-14-(t-butyldimethylsilyloxy)-6,16-bis-(p-methoxybenzyloxy)-5,7,9,11,13,15-hexamethyl-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,7S,8R,9S,11Z,13S,14R,15S)-14-(t-butyldimethylsilyloxy)-6,16-bis-(p-methoxybenzyloxy)-5,7,9,11,13,15-hexamethyl-hexadeca-1,3,11-trien-8-ol

There total 49 articles about (3Z,5S,6S,7S,8R,9S,11Z,13S,14R,15S)-14-(t-butyldimethylsilyloxy)-6,16-bis-(p-methoxybenzyloxy)-5,7,9,11,13,15-hexamethyl-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: 97.0%

(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 (373645-66-0) → (3Z,5S,6S,7S,8R,9S,11Z,13S,14R,15S)-14-(t-butyldimethylsilyloxy)-6,16-bis-(p-methoxybenzyloxy)-5,7,9,11,13,15-hexamethyl-hexadeca-1,3,11-trien-8-ol (261968-22-3)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at -78 - -10 ℃; for 2.5h;

DOI:10.1021/ja011211m

Reference yield:

(3Z,5S,6S,7R,8S,9R,11Z,13S,14R,15S)-14-(t-butyidimethylsilyloxy)-6,16-bis-(p-methoxybenzyloxy)-9-(2,4,6-trimethylphenyl)sulfoxymethyl-5,7,11,13,15-pentamethyl-hexadeca-1,3,11-trien-8-ol → (3Z,5S,6S,7S,8R,9S,11Z,13S,14R,15S)-14-(t-butyldimethylsilyloxy)-6,16-bis-(p-methoxybenzyloxy)-5,7,9,11,13,15-hexamethyl-hexadeca-1,3,11-trien-8-ol (261968-22-3)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at -78 - -10 ℃; for 1.5h;

Reference yield:

1-(p-methoxybenzyloxy)-5-hydroxy-2,4,6-trimethyl-6-hepten-3-one (261968-12-1) → (3Z,5S,6S,7S,8R,9S,11Z,13S,14R,15S)-14-(t-butyldimethylsilyloxy)-6,16-bis-(p-methoxybenzyloxy)-5,7,9,11,13,15-hexamethyl-hexadeca-1,3,11-trien-8-ol (261968-22-3)

Guidance literature:

Multi-step reaction with 13 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

13.1: 97 percent / LiAlH₄ / tetrahydrofuran / 2.5 h / -78 - -10 °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

upstream raw materials:

(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

(2R,3S,4S)-3-hydroxy-5-(4-methoxybenzyloxy)-2,4-dimethylpentanal

(2S,4S,5R)-6-(tert-butyldimethylsilyloxy)-5-hydroxy-1-(4-methoxybenzyloxy)-2,4-dimethylhexan-3-one

(2R,3R,4S,5S)-1-(tert-butyldimethylsilyloxy)-6-(4-methoxybenzyloxy)-3,5-dimethyl-hexane-2,4-diol

Downstream raw materials:

1-[(5Z,13Z)-(2S,3R,4S,8S,9R,10R,11S,12S)-11-(4-methoxybenzoxy)-3,9-bis(tert-butyldimethylsilanyloxy)-2,4,6,8,10,12-hexamethylhexadeca-5,13,15-trienyloxymethyl]-4-methoxybenzene

(3Z,5S,6S,7S,8R,9S,11Z,13S,14R,15S)-8,14-bis(t-butyldimethylsilyloxy)-6,16-bis-(p-methoxybenzyloxy)-5,7,9,11,13,15-hexamethyl-hexadeca-1,3,11-triene