(3S,4R,6R,7R,8R)-3-(tert-butyldimethylsilyloxy)-8-ethyl-7-(4-methoxybenzyloxy)-4,6-dimethyldec-9-en-1-ol

Base Information

• Chemical Name: (3S,4R,6R,7R,8R)-3-(tert-butyldimethylsilyloxy)-8-ethyl-7-(4-methoxybenzyloxy)-4,6-dimethyldec-9-en-1-ol
• CAS No.: 1312543-70-6
• Molecular Formula: C₂₈H₅₀O₄Si
• Molecular Weight: 478.788
• Mol file: 1312543-70-6.mol

Synonyms:(3S,4R,6R,7R,8R)-3-(tert-butyldimethylsilyloxy)-8-ethyl-7-(4-methoxybenzyloxy)-4,6-dimethyldec-9-en-1-ol

Chemical Property of (3S,4R,6R,7R,8R)-3-(tert-butyldimethylsilyloxy)-8-ethyl-7-(4-methoxybenzyloxy)-4,6-dimethyldec-9-en-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4R,6R,7R,8R)-3-(tert-butyldimethylsilyloxy)-8-ethyl-7-(4-methoxybenzyloxy)-4,6-dimethyldec-9-en-1-ol

There total 28 articles about (3S,4R,6R,7R,8R)-3-(tert-butyldimethylsilyloxy)-8-ethyl-7-(4-methoxybenzyloxy)-4,6-dimethyldec-9-en-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: 93.0%

C34H64O4Si2 (1312543-69-3) → (3S,4R,6R,7R,8R)-3-(tert-butyldimethylsilyloxy)-8-ethyl-7-(4-methoxybenzyloxy)-4,6-dimethyldec-9-en-1-ol (1312543-70-6)

Guidance literature:

With pyridine hydrogenfluoride; In tetrahydrofuran; at 0 - 20 ℃; for 20h; regioselective reaction; Inert atmosphere;

DOI:10.1039/c4ob00250d

Reference yield:

2-<(benzyloxy)-methyl>butyraldehyde (916501-75-2) → (3S,4R,6R,7R,8R)-3-(tert-butyldimethylsilyloxy)-8-ethyl-7-(4-methoxybenzyloxy)-4,6-dimethyldec-9-en-1-ol (1312543-70-6)

Guidance literature:

Multi-step reaction with 13 steps

1.1: tetrahydrofuran / 0 °C / Inert atmosphere

2.1: palladium on activated charcoal; hydrogen / 20 °C / 760.05 Torr

3.1: sodium hydride / N,N-dimethyl-formamide / Inert atmosphere; Heating

3.2: Inert atmosphere

4.1: Dess-Martin periodane / dichloromethane / 0 - 20 °C / Inert atmosphere

5.1: dicyclohexylboron chloride; triethylamine / diethyl ether / 2.5 h / -78 - 0 °C / Inert atmosphere

5.2: 14 h / -78 - -25 °C / Inert atmosphere

6.1: zinc(II) tetrahydroborate / dichloromethane; diethyl ether / 6 h / -40 °C

7.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 2 h / -10 °C / Molecular sieve; Inert atmosphere

8.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

8.2: 0.5 h / -78 °C / Inert atmosphere

8.3: 0.25 h / -78 °C / Inert atmosphere

9.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / 1 h / 120 °C / Inert atmosphere

10.1: diisobutylaluminium hydride / dichloromethane; toluene / 2 h / -40 °C / Inert atmosphere

11.1: triethylamine; sulfur trioxide pyridine complex / dichloromethane; dimethyl sulfoxide / 0 °C / Inert atmosphere

12.1: sodium hexamethyldisilazane / tetrahydrofuran / 18 h / -78 - 20 °C / Inert atmosphere

13.1: pyridine hydrogenfluoride / tetrahydrofuran / 20 h / 0 - 20 °C / Inert atmosphere

With zinc(II) tetrahydroborate; 2,2'-azobis(isobutyronitrile); palladium on activated charcoal; dicyclohexylboron chloride; hydrogen; tri-n-butyl-tin hydride; sodium hexamethyldisilazane; sulfur trioxide pyridine complex; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; pyridine hydrogenfluoride; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; diethyl ether; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; 1.1: |Grignard Reaction / 9.1: |Barton-McCombie Deoxygenation / 12.1: |Julia-Kocienski Olefination;

DOI:10.1039/c4ob00250d

Reference yield:

C14H22O2 → (3S,4R,6R,7R,8R)-3-(tert-butyldimethylsilyloxy)-8-ethyl-7-(4-methoxybenzyloxy)-4,6-dimethyldec-9-en-1-ol (1312543-70-6)

Guidance literature:

Multi-step reaction with 12 steps

1.1: palladium on activated charcoal; hydrogen / 20 °C / 760.05 Torr

2.1: sodium hydride / N,N-dimethyl-formamide / Inert atmosphere; Heating

2.2: Inert atmosphere

3.1: Dess-Martin periodane / dichloromethane / 0 - 20 °C / Inert atmosphere

4.1: dicyclohexylboron chloride; triethylamine / diethyl ether / 2.5 h / -78 - 0 °C / Inert atmosphere

4.2: 14 h / -78 - -25 °C / Inert atmosphere

5.1: zinc(II) tetrahydroborate / dichloromethane; diethyl ether / 6 h / -40 °C

6.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 2 h / -10 °C / Molecular sieve; Inert atmosphere

7.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

7.2: 0.5 h / -78 °C / Inert atmosphere

7.3: 0.25 h / -78 °C / Inert atmosphere

8.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / 1 h / 120 °C / Inert atmosphere

9.1: diisobutylaluminium hydride / dichloromethane; toluene / 2 h / -40 °C / Inert atmosphere

10.1: triethylamine; sulfur trioxide pyridine complex / dichloromethane; dimethyl sulfoxide / 0 °C / Inert atmosphere

11.1: sodium hexamethyldisilazane / tetrahydrofuran / 18 h / -78 - 20 °C / Inert atmosphere

12.1: pyridine hydrogenfluoride / tetrahydrofuran / 20 h / 0 - 20 °C / Inert atmosphere

With zinc(II) tetrahydroborate; 2,2'-azobis(isobutyronitrile); palladium on activated charcoal; dicyclohexylboron chloride; hydrogen; tri-n-butyl-tin hydride; sodium hexamethyldisilazane; sulfur trioxide pyridine complex; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; pyridine hydrogenfluoride; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; diethyl ether; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; 8.1: |Barton-McCombie Deoxygenation / 11.1: |Julia-Kocienski Olefination;

DOI:10.1039/c4ob00250d

upstream raw materials:

(2R)-2-[(4S,5S)-5-ethyl-2-(4-methoxyphenyl)-1,3-dioxan-4-yl]propan-1-ol

C₁₉H₃₀O₄

C₂₅H₄₄O₄Si

C₂₅H₄₆O₄Si

Downstream raw materials:

C₂₈H₄₈O₄Si

C₃₈H₅₈O₄Si

(1E,3E,7S,8R,10R,11R,12R)-7-(tert-butyldimethylsilyloxy)-12-ethyl-11-hydroxy-8,10-dimethyl-1-phenyltetradeca-1,3,13-trien-5-one

(3R,4R,5R,7R,8S,11E,13E)-8-(tert-butyldimethylsilyloxy)-3-ethyl-5,7-dimethyl-10-oxo-14-phenyltetradeca-1,11,13-trien-4-yl acrylate