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

Base Information

• Chemical Name: (2S,3S,5R,6R,8S)-3-(tert-butyldimethylsilyloxy)-9-(4-methoxyphenoxy)-2,5,8-trimethyl-5,6-bis[(triethylsilyl)oxy]nonanal
• CAS No.: 944943-21-9
• Molecular Formula: C₃₈H₇₄O₆Si₃
• Molecular Weight: 711.258
• Mol file: 944943-21-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 13 articles about (2S,3S,5R,6R,8S)-3-(tert-butyldimethylsilyloxy)-9-(4-methoxyphenoxy)-2,5,8-trimethyl-5,6-bis[(triethylsilyl)oxy]nonanal 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:

(2R,3S,5R,6R,8S)-3-(tert-butyldimethylsilyloxy)-9-(4-methoxyphenoxy)-2,5,8-trimethyl-5,6-bis[(triethylsilyl)oxy]nonan-1-ol (944943-19-5) → (2S,3S,5R,6R,8S)-3-(tert-butyldimethylsilyloxy)-9-(4-methoxyphenoxy)-2,5,8-trimethyl-5,6-bis[(triethylsilyl)oxy]nonanal (944943-21-9)

Guidance literature:

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

DOI:10.1021/ol0710360

Reference yield:

2-methyl-1-buten-4-ol (763-32-6) → (2S,3S,5R,6R,8S)-3-(tert-butyldimethylsilyloxy)-9-(4-methoxyphenoxy)-2,5,8-trimethyl-5,6-bis[(triethylsilyl)oxy]nonanal (944943-21-9)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 95 percent / triphenylphosphine; diisopropylazodicarboxylate / tetrahydrofuran / 3 h / Heating

2.1: 99 percent / AD-mix-β / H2O; 2-methyl-propan-2-ol / 4 h / 0 °C

3.1: 98 percent / triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 4 h / 20 °C

4.1: 81 percent / ammonium cerium(IV) nitrate / H₂O; acetonitrile / 0.17 h / 0 °C

5.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / -78 °C

6.1: 92 percent / EtMgBr / diethyl ether / 3 h / 20 °C

7.1: 95 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 1 h / 20 °C

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

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

9.2: CH₂Cl₂; hexane / -78 - 20 °C

9.3: methanol; hydrogen peroxide / CH₂Cl₂; hexane

10.1: 2,6-lutidine / CH₂Cl₂ / 3 h / -78 °C

11.1: diisobutylaluminum hydride / CH₂Cl₂; hexane / 3 h / -78 °C

12.1: 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; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; triethylamine; triphenylphosphine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; acetonitrile; tert-butyl alcohol; 7.1: Dess-Martin oxidation / 9.1: Dess-Martin oxidation / 13.1: Dess-Martin oxidation;

DOI:10.1021/ol0710360

Reference yield:

(R)-2-hydroxy-4-(4-methoxyphenoxy)-2-methylbutyl 2,2,2-trimethylacetate (237393-21-4) → (2S,3S,5R,6R,8S)-3-(tert-butyldimethylsilyloxy)-9-(4-methoxyphenoxy)-2,5,8-trimethyl-5,6-bis[(triethylsilyl)oxy]nonanal (944943-21-9)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 81 percent / ammonium cerium(IV) nitrate / H₂O; acetonitrile / 0.17 h / 0 °C

2.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / -78 °C

3.1: 92 percent / EtMgBr / diethyl ether / 3 h / 20 °C

4.1: 95 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 1 h / 20 °C

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

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

6.2: CH₂Cl₂; hexane / -78 - 20 °C

6.3: methanol; hydrogen peroxide / CH₂Cl₂; hexane

7.1: 2,6-lutidine / CH₂Cl₂ / 3 h / -78 °C

8.1: diisobutylaluminum hydride / CH₂Cl₂; hexane / 3 h / -78 °C

9.1: Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 1 h / 20 °C

With 2,6-dimethylpyridine; ammonium cerium(IV) nitrate; ethylmagnesium bromide; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; triethylamine; In diethyl ether; hexane; dichloromethane; water; acetonitrile; 4.1: Dess-Martin oxidation / 6.1: Dess-Martin oxidation / 10.1: Dess-Martin oxidation;

DOI:10.1021/ol0710360

upstream raw materials:

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

2-methyl-1-buten-4-ol

(R)-2-hydroxy-4-(4-methoxyphenoxy)-2-methylbutyl 2,2,2-trimethylacetate

(R)-2,4-dihydroxy-2-methylbutyl 2,2,2-trimethylacetate

Downstream raw materials:

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