[(E)-(3R,4S,5R,6R)-3,5,9-Tris-(tert-butyl-dimethyl-silanyloxy)-4,6,8-trimethyl-non-7-enyloxymethyl]-benzene

Base Information

• Chemical Name: [(E)-(3R,4S,5R,6R)-3,5,9-Tris-(tert-butyl-dimethyl-silanyloxy)-4,6,8-trimethyl-non-7-enyloxymethyl]-benzene
• CAS No.: 851592-67-1
• Molecular Formula: C₃₇H₇₂O₄Si₃
• Molecular Weight: 665.233
• Mol file: 851592-67-1.mol

Synonyms:[(E)-(3R,4S,5R,6R)-3,5,9-Tris-(tert-butyl-dimethyl-silanyloxy)-4,6,8-trimethyl-non-7-enyloxymethyl]-benzene

Chemical Property of [(E)-(3R,4S,5R,6R)-3,5,9-Tris-(tert-butyl-dimethyl-silanyloxy)-4,6,8-trimethyl-non-7-enyloxymethyl]-benzene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(E)-(3R,4S,5R,6R)-3,5,9-Tris-(tert-butyl-dimethyl-silanyloxy)-4,6,8-trimethyl-non-7-enyloxymethyl]-benzene

There total 13 articles about [(E)-(3R,4S,5R,6R)-3,5,9-Tris-(tert-butyl-dimethyl-silanyloxy)-4,6,8-trimethyl-non-7-enyloxymethyl]-benzene 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: 98.0%

(E)-(4R,5R,6S,7R)-9-Benzyloxy-5,7-bis-(tert-butyl-dimethyl-silanyloxy)-2,4,6-trimethyl-non-2-en-1-ol (881690-78-4) + tert-butyldimethylsilyl chloride (18162-48-6) → [(E)-(3R,4S,5R,6R)-3,5,9-Tris-(tert-butyl-dimethyl-silanyloxy)-4,6,8-trimethyl-non-7-enyloxymethyl]-benzene (851592-67-1)

Guidance literature:

With 1H-imidazole; dmap; In dichloromethane; at 0 ℃;

DOI:10.1002/anie.200462300

Reference yield:

(2R,3R)-3-(2-Benzyloxy-ethyl)-oxirane-2-carbaldehyde → [(E)-(3R,4S,5R,6R)-3,5,9-Tris-(tert-butyl-dimethyl-silanyloxy)-4,6,8-trimethyl-non-7-enyloxymethyl]-benzene (851592-67-1)

Guidance literature:

Multi-step reaction with 12 steps

1: NaH / tetrahydrofuran / 0 °C

2: 96 percent / D₂O; CH₂Cl₂ / -30 - -10 °C

3: imidazole; 4-(dimethylamino)pyridine / CH₂Cl₂ / 20 °C

4: diisobutylaluminum hydride / tetrahydrofuran / 0 °C

5: 88 percent / 3-chloroperoxybenzoic acid / CH₂Cl₂ / 0 °C

6: pyridinium dichromate; molecular sieves 4 Angstroem / 1,2-dichloro-ethane / 60 °C

7: 0 °C

8: tetrabutylammonium fluoride / tetrahydrofuran / 0 °C

9: 90 percent / D₂O; CH₂Cl₂ / -30 - -10 °C

10: 93 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

11: 98 percent / diisobutylaluminum hydride / tetrahydrofuran / 0 °C

12: 98 percent / imidazole; DMAP / CH₂Cl₂ / 0 °C

With 1H-imidazole; 2,6-dimethylpyridine; dmap; dipyridinium dichromate; 4 A molecular sieve; tetrabutyl ammonium fluoride; sodium hydride; diisobutylaluminium hydride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; water-d2; 1,2-dichloro-ethane; 1: Horner-Wadsworth-Emmons reaction / 7: Wittig reaction;

DOI:10.1002/anie.200462300

Reference yield:

(E)-3-[(2S,3R)-3-(2-Benzyloxy-ethyl)-oxiranyl]-acrylic acid ethyl ester (851592-61-5) → [(E)-(3R,4S,5R,6R)-3,5,9-Tris-(tert-butyl-dimethyl-silanyloxy)-4,6,8-trimethyl-non-7-enyloxymethyl]-benzene (851592-67-1)

Guidance literature:

Multi-step reaction with 11 steps

1: 96 percent / D₂O; CH₂Cl₂ / -30 - -10 °C

2: imidazole; 4-(dimethylamino)pyridine / CH₂Cl₂ / 20 °C

3: diisobutylaluminum hydride / tetrahydrofuran / 0 °C

4: 88 percent / 3-chloroperoxybenzoic acid / CH₂Cl₂ / 0 °C

5: pyridinium dichromate; molecular sieves 4 Angstroem / 1,2-dichloro-ethane / 60 °C

6: 0 °C

7: tetrabutylammonium fluoride / tetrahydrofuran / 0 °C

8: 90 percent / D₂O; CH₂Cl₂ / -30 - -10 °C

9: 93 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

10: 98 percent / diisobutylaluminum hydride / tetrahydrofuran / 0 °C

11: 98 percent / imidazole; DMAP / CH₂Cl₂ / 0 °C

With 1H-imidazole; 2,6-dimethylpyridine; dmap; dipyridinium dichromate; 4 A molecular sieve; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; water-d2; 1,2-dichloro-ethane; 6: Wittig reaction;

DOI:10.1002/anie.200462300

upstream raw materials:

(E)-(4R,5R,6S,7R)-9-Benzyloxy-5,7-bis-(tert-butyl-dimethyl-silanyloxy)-2,4,6-trimethyl-non-2-en-1-ol

tert-butyldimethylsilyl chloride

(E)-3-[(2S,3R)-3-(2-Benzyloxy-ethyl)-oxiranyl]-acrylic acid ethyl ester

(E)-(4R,5R)-7-Benzyloxy-5-hydroxy-4-methyl-hept-2-enoic acid ethyl ester

Downstream raw materials:

C₃₃H₄₃NO₉