(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

Base Information

• Chemical Name: (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
• CAS No.: 329189-00-6
• Molecular Formula: C₃₃H₅₆O₈Si
• Molecular Weight: 608.888

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 16 articles about (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 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:

(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-dien-1-ol → (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 (329189-00-6)

Guidance literature:

With manganese(IV) oxide; In hexane; chloroform; at 20 ℃;

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

Reference yield:

(E)-4-(t-butyl-dimethyl-silanyloxy)-2-methyl-but-2-enal (144950-82-3) → (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 (329189-00-6)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 78 percent / trifluoroacetic acid / (S)-BINOL; Ti(OiPr)4 / CH₂Cl₂ / 65 h / -78 - 20 °C

2.1: 97 percent / iPr₂NEt / tetrahydrofuran / 0 °C

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

3.2: 74 percent / NaIO₄ / tetrahydrofuran; H₂O / 20 °C

4.1: 52 percent / TiCl₄; iPr₂NEt / CH₂Cl₂ / -90 °C

5.1: 95 percent / HCl / methanol / 20 °C

6.1: imidazole / CH₂Cl₂ / 20 °C

7.1: iPr₂NEt / CH₂Cl₂ / 0 - 20 °C

8.1: SmI / methanol; tetrahydrofuran / 0 - 20 °C

9.1: iPr₂NEt / CH₂Cl₂ / 20 °C

10.1: HF*pyridine / tetrahydrofuran / 0 °C

11.1: MnO₂ / CHCl₃; hexane / 20 °C

With 1H-imidazole; hydrogenchloride; manganese(IV) oxide; osmium(VIII) oxide; samarium(II) iodide; titanium tetrachloride; pyridine hydrogenfluoride; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; titanium(IV) isopropylate; (S)-[1,1']-binaphthalenyl-2,2'-diol; In tetrahydrofuran; methanol; hexane; dichloromethane; chloroform; water; tert-butyl alcohol;

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

Reference yield:

p-methoxybenzyloxyacetaldehyde (121289-23-4) → (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 (329189-00-6)

Guidance literature:

Multi-step reaction with 10 steps

1: toluene / 80 °C

2: NH₄Cl / methanol

3: 52 percent / TiCl₄; iPr₂NEt / CH₂Cl₂ / -90 °C

4: 95 percent / HCl / methanol / 20 °C

5: imidazole / CH₂Cl₂ / 20 °C

6: iPr₂NEt / CH₂Cl₂ / 0 - 20 °C

7: SmI / methanol; tetrahydrofuran / 0 - 20 °C

8: iPr₂NEt / CH₂Cl₂ / 20 °C

9: HF*pyridine / tetrahydrofuran / 0 °C

10: MnO₂ / CHCl₃; hexane / 20 °C

With 1H-imidazole; hydrogenchloride; manganese(IV) oxide; samarium(II) iodide; titanium tetrachloride; ammonium chloride; pyridine hydrogenfluoride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; hexane; dichloromethane; chloroform; toluene;

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

upstream raw materials:

p-methoxybenzyloxyacetaldehyde

p-Methoxybenzyl bromide

1,4-bis<(4-methoxybenzyl)oxy>but-2-ene

(E)-4-(t-butyl-dimethyl-silanyloxy)-2-methyl-but-2-enal

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