(E)-(4R,5R,6S,7R)-9-Benzyloxy-5,7-dihydroxy-2,4,6-trimethyl-non-2-enoic acid ethyl ester

Base Information

• Chemical Name: (E)-(4R,5R,6S,7R)-9-Benzyloxy-5,7-dihydroxy-2,4,6-trimethyl-non-2-enoic acid ethyl ester
• CAS No.: 851592-66-0
• Molecular Formula: C₂₁H₃₂O₅
• Molecular Weight: 364.482
• Mol file: 851592-66-0.mol

Synonyms:(E)-(4R,5R,6S,7R)-9-Benzyloxy-5,7-dihydroxy-2,4,6-trimethyl-non-2-enoic acid ethyl ester

Chemical Property of (E)-(4R,5R,6S,7R)-9-Benzyloxy-5,7-dihydroxy-2,4,6-trimethyl-non-2-enoic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(4R,5R,6S,7R)-9-Benzyloxy-5,7-dihydroxy-2,4,6-trimethyl-non-2-enoic acid ethyl ester

There total 10 articles about (E)-(4R,5R,6S,7R)-9-Benzyloxy-5,7-dihydroxy-2,4,6-trimethyl-non-2-enoic acid ethyl ester 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: 90.0%

(E)-3-[(2S,3S)-3-((1S,2R)-4-Benzyloxy-2-hydroxy-1-methyl-butyl)-oxiranyl]-2-methyl-acrylic acid ethyl ester (851592-65-9) + trimethylaluminum (75-24-1) → (E)-(4R,5R,6S,7R)-9-Benzyloxy-5,7-dihydroxy-2,4,6-trimethyl-non-2-enoic acid ethyl ester (851592-66-0)

Guidance literature:

In dichloromethane; water-d2; at -30 - -10 ℃;

DOI:10.1002/anie.200462300

Reference yield:

(2R,3R)-3-(2-Benzyloxy-ethyl)-oxirane-2-carbaldehyde → (E)-(4R,5R,6S,7R)-9-Benzyloxy-5,7-dihydroxy-2,4,6-trimethyl-non-2-enoic acid ethyl ester (851592-66-0)

Guidance literature:

Multi-step reaction with 9 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

With 1H-imidazole; 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)-(4R,5R,6S,7R)-9-Benzyloxy-5,7-dihydroxy-2,4,6-trimethyl-non-2-enoic acid ethyl ester (851592-66-0)

Guidance literature:

Multi-step reaction with 8 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

With 1H-imidazole; 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)-3-[(2S,3S)-3-((1S,2R)-4-Benzyloxy-2-hydroxy-1-methyl-butyl)-oxiranyl]-2-methyl-acrylic acid ethyl ester

trimethylaluminum

(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:

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

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

C₃₃H₄₃NO₉

(E)-(4R,5R,6S,7R)-9-Benzyloxy-5,7-bis-(tert-butyl-dimethyl-silanyloxy)-2,4,6-trimethyl-non-2-enoic acid ethyl ester