(2E,9E)-(4R,5R,8S)-8,11-Bis-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-1-(4-methoxy-benzyloxy)-3,5,9-trimethyl-undeca-2,9-dien-6-one

Base Information

• Chemical Name: (2E,9E)-(4R,5R,8S)-8,11-Bis-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-1-(4-methoxy-benzyloxy)-3,5,9-trimethyl-undeca-2,9-dien-6-one
• CAS No.: 329188-97-8
• Molecular Formula: C₃₅H₆₂O₆Si₂
• Molecular Weight: 635.045

Synonyms:(2E,9E)-(4R,5R,8S)-8,11-Bis-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-1-(4-methoxy-benzyloxy)-3,5,9-trimethyl-undeca-2,9-dien-6-one

Chemical Property of (2E,9E)-(4R,5R,8S)-8,11-Bis-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-1-(4-methoxy-benzyloxy)-3,5,9-trimethyl-undeca-2,9-dien-6-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Useful:

Technology Process of (2E,9E)-(4R,5R,8S)-8,11-Bis-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-1-(4-methoxy-benzyloxy)-3,5,9-trimethyl-undeca-2,9-dien-6-one

There total 11 articles about (2E,9E)-(4R,5R,8S)-8,11-Bis-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-1-(4-methoxy-benzyloxy)-3,5,9-trimethyl-undeca-2,9-dien-6-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: 52.0%

1-({[(2E)-4,4-dimethoxy-3-methylbut-2-en-1-yl]oxy}methyl)-4-methoxybenzene (329188-96-7) + (E)-(S)-5,8-Bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-oct-6-en-3-one (329188-95-6) → (2E,9E)-(4R,5R,8S)-8,11-Bis-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-1-(4-methoxy-benzyloxy)-3,5,9-trimethyl-undeca-2,9-dien-6-one (329188-97-8)

Guidance literature:

With titanium tetrachloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at -90 ℃;

DOI:10.1002/1521-3773(20010105)40:1<231::AID-ANIE231>3.0.CO;2-W

Reference yield:

tert-butyldimethylsiloxyacetaldehyde (102191-92-4) → (2E,9E)-(4R,5R,8S)-8,11-Bis-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-1-(4-methoxy-benzyloxy)-3,5,9-trimethyl-undeca-2,9-dien-6-one (329188-97-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: toluene / 80 °C

2.1: 78 percent / trifluoroacetic acid / (S)-BINOL; Ti(OiPr)4 / CH₂Cl₂ / 65 h / -78 - 20 °C

3.1: 97 percent / iPr₂NEt / tetrahydrofuran / 0 °C

4.1: OsO₄; N-methylmorpholine N-oxide / 2-methyl-propan-2-ol; tetrahydrofuran; H₂O / 20 °C

4.2: 74 percent / NaIO₄ / tetrahydrofuran; H₂O / 20 °C

5.1: 52 percent / TiCl₄; iPr₂NEt / CH₂Cl₂ / -90 °C

With osmium(VIII) oxide; titanium tetrachloride; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; titanium(IV) isopropylate; (S)-[1,1']-binaphthalenyl-2,2'-diol; In tetrahydrofuran; dichloromethane; water; toluene; tert-butyl alcohol;

DOI:10.1002/1521-3773(20010105)40:1<231::AID-ANIE231>3.0.CO;2-W

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (2E,9E)-(4R,5R,8S)-8,11-Bis-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-1-(4-methoxy-benzyloxy)-3,5,9-trimethyl-undeca-2,9-dien-6-one (329188-97-8)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 99 percent / imidazole / CH₂Cl₂ / 0 °C

2.1: O₃ / CH₂Cl₂ / -78 °C

2.2: Ph₃P / CH₂Cl₂ / 20 °C

3.1: toluene / 80 °C

4.1: 78 percent / trifluoroacetic acid / (S)-BINOL; Ti(OiPr)4 / CH₂Cl₂ / 65 h / -78 - 20 °C

5.1: 97 percent / iPr₂NEt / tetrahydrofuran / 0 °C

6.1: OsO₄; N-methylmorpholine N-oxide / 2-methyl-propan-2-ol; tetrahydrofuran; H₂O / 20 °C

6.2: 74 percent / NaIO₄ / tetrahydrofuran; H₂O / 20 °C

7.1: 52 percent / TiCl₄; iPr₂NEt / CH₂Cl₂ / -90 °C

With 1H-imidazole; osmium(VIII) oxide; titanium tetrachloride; ozone; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; titanium(IV) isopropylate; (S)-[1,1']-binaphthalenyl-2,2'-diol; In tetrahydrofuran; dichloromethane; water; toluene; tert-butyl alcohol;

DOI:10.1002/1521-3773(20010105)40:1<231::AID-ANIE231>3.0.CO;2-W

upstream raw materials:

1-({[(2E)-4,4-dimethoxy-3-methylbut-2-en-1-yl]oxy}methyl)-4-methoxybenzene

(E)-(S)-5,8-Bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-oct-6-en-3-one

p-methoxybenzyloxyacetaldehyde

tert-butyldimethylsiloxyacetaldehyde

Downstream raw materials:

1-[(2E,9E)-(4R,5R,6S,8S)-6,11-Bis-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-8-(2-methoxy-ethoxymethoxy)-3,5,9-trimethyl-undeca-2,9-dienyloxymethyl]-4-methoxy-benzene

(2E,9E,5S,6S,8S,4R)-4-methoxy-8-[(2-methoxyethoxy)methoxy]-1-[(4-methoxyphenyl)methoxy]-3,5,9-trimethyl-11-(1,1,2,2-tetramethyl-1-silapropoxy)undeca-2,9-dien-6-ol

(2E,9E,8S,4R,5R)-4-methoxy-8-[(2-methoxyethoxy)methoxy]-1-[(4-methoxyphenyl)methoxy]-3,5,9-trimethyl-11-(1,1,2,2-tetramethyl-1-silapropoxy)undeca-2,9-dien-6-one

(2E,9E)-(4S,6S,7R,8R)-6-(tert-Butyl-dimethyl-silanyloxy)-8-methoxy-11-(4-methoxy-benzyloxy)-4-(2-methoxy-ethoxymethoxy)-3,7,9-trimethyl-undeca-2,9-dienal

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