(3R,4R,6S)-7-(4-methoxyphenoxy)-3,6-dimethyl-3,4-bis[(triethylsilyl)oxy]heptan-1-ol

Base Information

• Chemical Name: (3R,4R,6S)-7-(4-methoxyphenoxy)-3,6-dimethyl-3,4-bis[(triethylsilyl)oxy]heptan-1-ol
• CAS No.: 944943-11-7
• Molecular Formula: C₂₉H₅₆O₅Si₂
• Molecular Weight: 540.932
• Mol file: 944943-11-7.mol

Synonyms:(3R,4R,6S)-7-(4-methoxyphenoxy)-3,6-dimethyl-3,4-bis[(triethylsilyl)oxy]heptan-1-ol

Chemical Property of (3R,4R,6S)-7-(4-methoxyphenoxy)-3,6-dimethyl-3,4-bis[(triethylsilyl)oxy]heptan-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4R,6S)-7-(4-methoxyphenoxy)-3,6-dimethyl-3,4-bis[(triethylsilyl)oxy]heptan-1-ol

There total 8 articles about (3R,4R,6S)-7-(4-methoxyphenoxy)-3,6-dimethyl-3,4-bis[(triethylsilyl)oxy]heptan-1-ol 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:

2-methyl-1-buten-4-ol (763-32-6) → (3R,4R,6S)-7-(4-methoxyphenoxy)-3,6-dimethyl-3,4-bis[(triethylsilyl)oxy]heptan-1-ol (944943-11-7)

Guidance literature:

Multi-step reaction with 8 steps

1: 95 percent / triphenylphosphine; diisopropylazodicarboxylate / tetrahydrofuran / 3 h / Heating

2: 99 percent / AD-mix-β / H2O; 2-methyl-propan-2-ol / 4 h / 0 °C

3: 98 percent / triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 4 h / 20 °C

4: 81 percent / ammonium cerium(IV) nitrate / H₂O; acetonitrile / 0.17 h / 0 °C

5: 97 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / -78 °C

6: 92 percent / EtMgBr / diethyl ether / 3 h / 20 °C

7: 95 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 1 h / 20 °C

With 2,6-dimethylpyridine; dmap; ammonium cerium(IV) nitrate; di-isopropyl azodicarboxylate; AD-mix-β; ethylmagnesium bromide; sodium hydrogencarbonate; Dess-Martin periodane; triethylamine; triphenylphosphine; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetonitrile; tert-butyl alcohol; 7: Dess-Martin oxidation;

DOI:10.1021/ol0710360

Reference yield:

(R)-2,4-dihydroxy-2-methylbutyl 2,2,2-trimethylacetate (944943-06-0) → (3R,4R,6S)-7-(4-methoxyphenoxy)-3,6-dimethyl-3,4-bis[(triethylsilyl)oxy]heptan-1-ol (944943-11-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 97 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / -78 °C

2: 92 percent / EtMgBr / diethyl ether / 3 h / 20 °C

3: 95 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 1 h / 20 °C

With 2,6-dimethylpyridine; ethylmagnesium bromide; sodium hydrogencarbonate; Dess-Martin periodane; In diethyl ether; dichloromethane; 3: Dess-Martin oxidation;

DOI:10.1021/ol0710360

Reference yield:

(R)-2-hydroxy-4-(4-methoxyphenoxy)-2-methylbutyl 2,2,2-trimethylacetate (237393-21-4) → (3R,4R,6S)-7-(4-methoxyphenoxy)-3,6-dimethyl-3,4-bis[(triethylsilyl)oxy]heptan-1-ol (944943-11-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 81 percent / ammonium cerium(IV) nitrate / H₂O; acetonitrile / 0.17 h / 0 °C

2: 97 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / -78 °C

3: 92 percent / EtMgBr / diethyl ether / 3 h / 20 °C

4: 95 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 1 h / 20 °C

With 2,6-dimethylpyridine; ammonium cerium(IV) nitrate; ethylmagnesium bromide; sodium hydrogencarbonate; Dess-Martin periodane; In diethyl ether; dichloromethane; water; acetonitrile; 4: Dess-Martin oxidation;

DOI:10.1021/ol0710360

upstream raw materials:

(R)-2-methyl-2,4-bis[(triethylsilyl)oxy]butyraldehyde

triethylsilyl trifluoromethyl sulfonate

(R)-(+)-1-[(3'-iodo-2'-methylpropoxy)methyl]-4-methoxybenzene

2-methyl-1-buten-4-ol

Downstream raw materials:

(3R,4R,6S)-7-(4-methoxyphenoxy)-3,6-dimethyl-3,4-bis[(triethylsilyl)oxy]heptaldehyde

(3R,4S,6R,7R,9S)-4-(tert-butyldimethylsilyloxy)-10-(4-methoxyphenoxy)-3,6,9-trimethyl-6,7-bis[(triethylsilyl)oxy]dec-1-ene

(2S,3S,5R,6R,8S)-3-(tert-butyldimethylsilyloxy)-9-(4-methoxyphenoxy)-2,5,8-trimethyl-5,6-bis[(triethylsilyl)oxy]nonanal

(2R,3S,5R,6R,8S)-3-(tert-butyldimethylsilyloxy)-9-(4-methoxyphenoxy)-2,5,8-trimethyl-5,6-bis[(triethylsilyl)oxy]nonan-1-ol