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

Base Information

• Chemical Name: (3R,4S,6S)-7-(4-methoxyphenoxy)-3,6-dimethyl-3,4-bis[(triethylsilyl)oxy]heptan-1-ol
• CAS No.: 944942-96-5
• Molecular Formula: C₂₉H₅₆O₅Si₂
• Molecular Weight: 540.932
• Mol file: 944942-96-5.mol

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

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

There total 1 articles about (3R,4S,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:

(R)-2-methyl-2,4-bis[(triethylsilyl)oxy]butyraldehyde (944942-95-4) + triethylsilyl trifluoromethyl sulfonate (79271-56-0) + (R)-(+)-1-[(3'-iodo-2'-methylpropoxy)methyl]-4-methoxybenzene (183894-33-9) → (3R,4R,6S)-7-(4-methoxyphenoxy)-3,6-dimethyl-3,4-bis[(triethylsilyl)oxy]heptan-1-ol (944943-11-7) + (3R,4S,6S)-7-(4-methoxyphenoxy)-3,6-dimethyl-3,4-bis[(triethylsilyl)oxy]heptan-1-ol (944942-96-5)

Guidance literature:

Multistep reaction.;

DOI:10.1021/ol0710360

Reference yield: 94.0%

(3R,4S,6S)-7-(4-methoxyphenoxy)-3,6-dimethyl-3,4-bis[(triethylsilyl)oxy]heptan-1-ol (944942-96-5) → (3R,4S,6S)-7-(4-methoxyphenoxy)-3,6-dimethyl-3,4-bis[(triethylsilyl)oxy]heptaldehyde (944943-12-8)

Guidance literature:

With sodium hydrogencarbonate; Dess-Martin periodane; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1021/ol0710360

Reference yield:

(3R,4S,6S)-7-(4-methoxyphenoxy)-3,6-dimethyl-3,4-bis[(triethylsilyl)oxy]heptan-1-ol (944942-96-5) → C46H78O6Si2

Guidance literature:

Multi-step reaction with 14 steps

1.1: 94 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 1 h / 20 °C

2.1: triethylamine / CH₂Cl₂; hexane / 1 h / -78 °C

2.2: CH₂Cl₂; hexane / -78 - 20 °C

2.3: 84 percent / methanol; hydrogen peroxide / CH₂Cl₂; hexane

3.1: 96 percent / 2,6-lutidine / CH₂Cl₂ / 3 h / -78 °C

4.1: 80 percent / diisobutylaluminum hydride / CH₂Cl₂; hexane / 3 h / -78 °C

5.1: 96 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 1 h / 20 °C

6.1: 93 percent / potassium hexamethyldisilazide / tetrahydrofuran; toluene / -10 - 0 °C

7.1: 91 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂ / 0.33 h / 20 °C / pH 7

8.1: 96 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 1 h / 20 °C

9.1: 91 percent / CH₂Cl₂ / 72 h / 20 °C

10.1: 85 percent / potassium trimethylsilanolate / tetrahydrofuran / 9 h / 20 °C

11.1: 80 percent / triethylamine; 2,4,6-trichlorobenzoyl chloride; 4-(dimethylamino)pyridine / toluene / 1 h / 20 °C

12.1: 41 percent / trifluoroacetic acid / H₂O; tetrahydrofuran / 6 h / 20 °C

13.1: 93 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 1 h / 20 °C

14.1: 40 percent / Grubbs' 2nd generation catalyst / CH₂Cl₂ / 72 h / Heating

With 2,6-dimethylpyridine; dmap; 2,4,6-trichlorobenzoyl chloride; potassium trimethylsilonate; potassium hexamethylsilazane; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; triethylamine; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; hexane; dichloromethane; water; toluene; 1.1: Dess-Martin oxidation / 5.1: Dess-Martin oxidation / 8.1: Dess-Martin oxidation / 13.1: 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

Downstream raw materials:

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

(1S,2R)-2-[benzyl(mesitylenyl)sulfonylamino]-1-phenylpropyl (2S,3S,5R,6S,8S)-3-hydroxy-9-(4-methoxyphenoxy)-2,5,8-trimethyl-5,6-bis[(triethylsilyl)oxy]nonanoate

(1S,2R)-2-[benzyl(mesitylenyl)sulfonylamino]-1-phenylpropyl (2S,3S,5R,6S,8S)-3-(tert-butyldimethylsilyloxy)-9-(4-methoxyphenoxy)-2,5,8-trimethyl-5,6-bis[(triethylsilyl)oxy]nonanoate

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