2R,10R-bis-(tert-butyldimethylsiloxy)-3S,5S,7R,9S-tetramethyl-11-benzyloxy-1-hydroxy-undecene

Base Information

• Chemical Name: 2R,10R-bis-(tert-butyldimethylsiloxy)-3S,5S,7R,9S-tetramethyl-11-benzyloxy-1-hydroxy-undecene
• CAS No.: 501419-29-0
• Molecular Formula: C₃₄H₆₆O₄Si₂
• Molecular Weight: 595.067
• Mol file: 501419-29-0.mol

Synonyms:2R,10R-bis-(tert-butyldimethylsiloxy)-3S,5S,7R,9S-tetramethyl-11-benzyloxy-1-hydroxy-undecene

Chemical Property of 2R,10R-bis-(tert-butyldimethylsiloxy)-3S,5S,7R,9S-tetramethyl-11-benzyloxy-1-hydroxy-undecene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2R,10R-bis-(tert-butyldimethylsiloxy)-3S,5S,7R,9S-tetramethyl-11-benzyloxy-1-hydroxy-undecene

There total 29 articles about 2R,10R-bis-(tert-butyldimethylsiloxy)-3S,5S,7R,9S-tetramethyl-11-benzyloxy-1-hydroxy-undecene 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: 98.0%

2R,10R-bis-(tert-butyldimethylsiloxy)-3S,5S,7R,9S-tetramethyl-11-benzyloxy-1-paramethoxybenzyloxy-undecene (501419-28-9) → 2R,10R-bis-(tert-butyldimethylsiloxy)-3S,5S,7R,9S-tetramethyl-11-benzyloxy-1-hydroxy-undecene (501419-29-0)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In aq. phosphate buffer; dichloromethane; for 1h; pH=7; Inert atmosphere;

DOI:10.1246/bcsj.20180292

Reference yield:

(+)-(2S,3R)-4-benzyloxy-3-(tert-butyldimethylsiloxy)-2-methylbutan-1-ol (501419-25-6) → 2R,10R-bis-(tert-butyldimethylsiloxy)-3S,5S,7R,9S-tetramethyl-11-benzyloxy-1-hydroxy-undecene (501419-29-0)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 96 percent / triphenylphosphine; iodine; imidazole / acetonitrile; diethyl ether / 20 °C

2.1: LiCl; diisopropylamine; n-butyllithium / tetrahydrofuran; petroleum ether / 1.33 h / -78 - 20 °C

2.2: 93 percent / tetrahydrofuran; various solvent(s) / 40 h / 0 °C

3.1: 93 percent / diisopropylamine; n-butyllithium; borane-ammonium complex / tetrahydrofuran; petroleum ether / 2.17 h / 0 - 20 °C

4.1: 95 percent / triphenylphosphine; imidazole; iodine / diethyl ether; acetonitrile / 0.17 h / 20 °C

5.1: tert-butyllithium; ZnCl₂ / diethyl ether; petroleum ether / 1 h / 20 °C

5.2: 58 percent / Pd(PPh₃)4 / diethyl ether; various solvent(s) / 16 h

6.1: 87 percent / TBAF / tetrahydrofuran / 20 h / 20 °C

7.1: 86 percent / H₂ / Rh[(nbd)dppb]BF₄ / CH₂Cl₂ / 4 h / 36201.3 Torr

8.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 20 °C

9.1: 93 percent / DDQ / CH₂Cl₂ / 1 h / 20 °C / pH 7

With 1H-imidazole; 2,6-dimethylpyridine; n-butyllithium; tetrabutyl ammonium fluoride; hydrogen; iodine; tert.-butyl lithium; diisopropylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium chloride; zinc(II) chloride; {(1,4-bis(diphenylphosphino)butane)Rh(norbornadiene)}BF₄; In tetrahydrofuran; diethyl ether; dichloromethane; acetonitrile; Petroleum ether; 2.1: Myer's alkylation / 5.2: Negishi coupling;

DOI:10.1021/ja028941u

Reference yield:

4-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-butyric acid methyl ester (501419-24-5) → 2R,10R-bis-(tert-butyldimethylsiloxy)-3S,5S,7R,9S-tetramethyl-11-benzyloxy-1-hydroxy-undecene (501419-29-0)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 94 percent / DIBAL-H / CH₂Cl₂ / 1.25 h / -78 - 0 °C

2.1: 96 percent / triphenylphosphine; iodine; imidazole / acetonitrile; diethyl ether / 20 °C

3.1: LiCl; diisopropylamine; n-butyllithium / tetrahydrofuran; petroleum ether / 1.33 h / -78 - 20 °C

3.2: 93 percent / tetrahydrofuran; various solvent(s) / 40 h / 0 °C

4.1: 93 percent / diisopropylamine; n-butyllithium; borane-ammonium complex / tetrahydrofuran; petroleum ether / 2.17 h / 0 - 20 °C

5.1: 95 percent / triphenylphosphine; imidazole; iodine / diethyl ether; acetonitrile / 0.17 h / 20 °C

6.1: tert-butyllithium; ZnCl₂ / diethyl ether; petroleum ether / 1 h / 20 °C

6.2: 58 percent / Pd(PPh₃)4 / diethyl ether; various solvent(s) / 16 h

7.1: 87 percent / TBAF / tetrahydrofuran / 20 h / 20 °C

8.1: 86 percent / H₂ / Rh[(nbd)dppb]BF₄ / CH₂Cl₂ / 4 h / 36201.3 Torr

9.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 20 °C

10.1: 93 percent / DDQ / CH₂Cl₂ / 1 h / 20 °C / pH 7

With 1H-imidazole; 2,6-dimethylpyridine; n-butyllithium; tetrabutyl ammonium fluoride; hydrogen; iodine; tert.-butyl lithium; diisobutylaluminium hydride; diisopropylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium chloride; zinc(II) chloride; {(1,4-bis(diphenylphosphino)butane)Rh(norbornadiene)}BF₄; In tetrahydrofuran; diethyl ether; dichloromethane; acetonitrile; Petroleum ether; 3.1: Myer's alkylation / 6.2: Negishi coupling;

DOI:10.1021/ja028941u

upstream raw materials:

2R,10R-bis-(tert-butyldimethylsiloxy)-3S,5S,7R,9S-tetramethyl-11-benzyloxy-1-paramethoxybenzyloxy-undecene

(+)-(2S,3R)-4-benzyloxy-3-(tert-butyldimethylsiloxy)-2-methylbutan-1-ol

4-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-butyric acid methyl ester

(2S,3R)-3-{[tert-butyl(dimethyl)silyl]oxy}-4-[(4-methoxybenzyl)oxy]-2-methylbutan-1-ol

Downstream raw materials:

C₃₅H₆₈O₆SSi₂

12-benzyloxy-3S,11R-dihydroxy-4S,6S,8R,10S-tetramethyl-dodecanenitrile

12-benzyloxy-3S,11R-bis-methoxymethoxy-4S,6S,8R,10S-tetramethyl-dodecanenitrile

C₂₇H₄₆O₆