(E)-(2R,6R,7S)-2,6-Dimethyl-7-[4-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-pentadecafluoro-decyloxy)-benzyloxy]-oct-4-enal

Base Information

• Chemical Name: (E)-(2R,6R,7S)-2,6-Dimethyl-7-[4-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-pentadecafluoro-decyloxy)-benzyloxy]-oct-4-enal
• CAS No.: 780772-51-2
• Molecular Formula: C₂₇H₂₉F₁₅O₃
• Molecular Weight: 686.502
• Mol file: 780772-51-2.mol

Synonyms:(E)-(2R,6R,7S)-2,6-Dimethyl-7-[4-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-pentadecafluoro-decyloxy)-benzyloxy]-oct-4-enal

Chemical Property of (E)-(2R,6R,7S)-2,6-Dimethyl-7-[4-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-pentadecafluoro-decyloxy)-benzyloxy]-oct-4-enal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(2R,6R,7S)-2,6-Dimethyl-7-[4-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-pentadecafluoro-decyloxy)-benzyloxy]-oct-4-enal

There total 16 articles about (E)-(2R,6R,7S)-2,6-Dimethyl-7-[4-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-pentadecafluoro-decyloxy)-benzyloxy]-oct-4-enal 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:

(3R)-4-(tert-butyldimethylsilanyloxy)-3-methylbutan-1-ol (147915-55-7) → (E)-(2R,6R,7S)-2,6-Dimethyl-7-[4-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-pentadecafluoro-decyloxy)-benzyloxy]-oct-4-enal (780772-51-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 88 percent / diethyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 48 h / 20 °C

2.1: 89 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 36 h / 20 °C

3.1: sodium hexamethyldisilazide / tetrahydrofuran / -78 °C

3.2: tetrahydrofuran / -78 °C

4.1: TBAF / tetrahydrofuran / 3 h / 20 °C

5.1: Dess-Martin periodinane / CH₂Cl₂ / 3 h / 20 °C

With tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; Dess-Martin periodane; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; 1.1: Mitsunobu reaction / 3.2: Kocienski-Julia olefination / 5.1: Dess-Martin oxidation;

DOI:10.1021/jo051526a

Reference yield:

(3R)-4-(tert-butyldimethylsilanyloxy)-3-methylbutyraldehyde (156757-31-2) → (E)-(2R,6R,7S)-2,6-Dimethyl-7-[4-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-pentadecafluoro-decyloxy)-benzyloxy]-oct-4-enal (780772-51-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 97 percent / sodium borohydride / methanol; H₂O / 1 h / -20 °C

2.1: 88 percent / diethyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 48 h / 20 °C

3.1: 89 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 36 h / 20 °C

4.1: sodium hexamethyldisilazide / tetrahydrofuran / -78 °C

4.2: tetrahydrofuran / -78 °C

5.1: TBAF / tetrahydrofuran / 3 h / 20 °C

6.1: Dess-Martin periodinane / CH₂Cl₂ / 3 h / 20 °C

With sodium tetrahydroborate; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; Dess-Martin periodane; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; water; 2.1: Mitsunobu reaction / 4.2: Kocienski-Julia olefination / 6.1: Dess-Martin oxidation;

DOI:10.1021/jo051526a

Reference yield:

(3R)-4-(tert-butyldimethylsilanyloxy)-3-methylbutyronitrile (172668-98-3) → (E)-(2R,6R,7S)-2,6-Dimethyl-7-[4-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-pentadecafluoro-decyloxy)-benzyloxy]-oct-4-enal (780772-51-2)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 93 percent / DIBAL / CH₂Cl₂; hexane / 2 h / -20 °C

2.1: 97 percent / sodium borohydride / methanol; H₂O / 1 h / -20 °C

3.1: 88 percent / diethyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 48 h / 20 °C

4.1: 89 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 36 h / 20 °C

5.1: sodium hexamethyldisilazide / tetrahydrofuran / -78 °C

5.2: tetrahydrofuran / -78 °C

6.1: TBAF / tetrahydrofuran / 3 h / 20 °C

7.1: Dess-Martin periodinane / CH₂Cl₂ / 3 h / 20 °C

With sodium tetrahydroborate; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; diisobutylaluminium hydride; Dess-Martin periodane; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; hexane; dichloromethane; water; 3.1: Mitsunobu reaction / 5.2: Kocienski-Julia olefination / 7.1: Dess-Martin oxidation;

DOI:10.1021/jo051526a

upstream raw materials:

(E)-(2R,6R,7S)-2,6-Dimethyl-7-[4-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-pentadecafluoro-decyloxy)-benzyloxy]-oct-4-en-1-ol

(3R)-2-[4-(tert-butyldimethylsilanyloxy)-3-methylbutylsulfanyl]benzothiazole

(3R)-2-[4-(tert-butyldimethylsilanyloxy)-3-methylbutane-1-sulfonyl]benzothiazole

(3R)-5-[4-(tert-butyldimethylsilanyloxy)-3-methylbutane-1-sulfonyl]-1-phenyl-1H-tetrazole

Downstream raw materials:

(1S,2R,6S,10S)-1-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-pentadecafluorodecyloxy)-4-(1,2,6,10-tetramethyldodecyloxymethyl)benzene

(1S,2R,6S,10R)-1-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-pentadecafluorodecyloxy)-4-(1,2,6,10-tetramethyldodecyloxymethyl)benzene

(4E,8E)-(2R,6R,10R,11S)-2,6,10-Trimethyl-11-[4-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-pentadecafluoro-decyloxy)-benzyloxy]-dodeca-4,8-dien-1-ol

1-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-Pentadecafluoro-decyloxy)-4-((3E,7E)-(1S,2R,6R,10R)-1,2,6,10-tetramethyl-dodeca-3,7,11-trienyloxymethyl)-benzene