Dodecanenitrile, 3,11-bis(methoxymethoxy)-4,6,8,10-tetramethyl-12-(phenylmethoxy)-, (3S,4S,6S,8R,10S,11R)-

Base Information

• Chemical Name: Dodecanenitrile, 3,11-bis(methoxymethoxy)-4,6,8,10-tetramethyl-12-(phenylmethoxy)-, (3S,4S,6S,8R,10S,11R)-
• CAS No.: 501419-34-7
• Molecular Formula: C27H45NO5
• Molecular Weight: 463.658

Synonyms:

Chemical Property of Dodecanenitrile, 3,11-bis(methoxymethoxy)-4,6,8,10-tetramethyl-12-(phenylmethoxy)-, (3S,4S,6S,8R,10S,11R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Dodecanenitrile, 3,11-bis(methoxymethoxy)-4,6,8,10-tetramethyl-12-(phenylmethoxy)-, (3S,4S,6S,8R,10S,11R)-

There total 23 articles about Dodecanenitrile, 3,11-bis(methoxymethoxy)-4,6,8,10-tetramethyl-12-(phenylmethoxy)-, (3S,4S,6S,8R,10S,11R)- 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:

(+)-(2S,3R)-4-benzyloxy-3-(tert-butyldimethylsiloxy)-2-methylbutan-1-ol (501419-25-6) → 12-benzyloxy-3S,11R-bis-methoxymethoxy-4S,6S,8R,10S-tetramethyl-dodecanenitrile (501419-34-7)

Guidance literature:

Multi-step reaction with 14 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

10.1: triethylamine / CH₂Cl₂ / 1.5 h / 20 °C

11.1: HF / acetonitrile / 3 h / 20 °C

12.1: 98 percent / potassium carbonate / methanol / 0.75 h

13.1: 92 percent / lithium perchlorate / acetonitrile / 24 h / 70 °C

14.1: 81 percent / diisopropylethylamine / CH₂Cl₂ / 28 h / 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; n-butyllithium; hydrogen fluoride; tetrabutyl ammonium fluoride; hydrogen; iodine; tert.-butyl lithium; lithium perchlorate; potassium carbonate; triethylamine; diisopropylamine; N-ethyl-N,N-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; methanol; 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) → 12-benzyloxy-3S,11R-bis-methoxymethoxy-4S,6S,8R,10S-tetramethyl-dodecanenitrile (501419-34-7)

Guidance literature:

Multi-step reaction with 15 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

11.1: triethylamine / CH₂Cl₂ / 1.5 h / 20 °C

12.1: HF / acetonitrile / 3 h / 20 °C

13.1: 98 percent / potassium carbonate / methanol / 0.75 h

14.1: 92 percent / lithium perchlorate / acetonitrile / 24 h / 70 °C

15.1: 81 percent / diisopropylethylamine / CH₂Cl₂ / 28 h / 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; n-butyllithium; hydrogen fluoride; tetrabutyl ammonium fluoride; hydrogen; iodine; tert.-butyl lithium; lithium perchlorate; diisobutylaluminium hydride; potassium carbonate; triethylamine; diisopropylamine; N-ethyl-N,N-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; methanol; diethyl ether; dichloromethane; acetonitrile; Petroleum ether; 3.1: Myer's alkylation / 6.2: Negishi coupling;

DOI:10.1021/ja028941u

Reference yield:

5R-tert-butyldimethylsiloxy-2S,4S-dimethyl-6-benzyloxy-hexanol (501419-26-7) → 12-benzyloxy-3S,11R-bis-methoxymethoxy-4S,6S,8R,10S-tetramethyl-dodecanenitrile (501419-34-7)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 95 percent / triphenylphosphine; imidazole; iodine / diethyl ether; acetonitrile / 0.17 h / 20 °C

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

2.2: 58 percent / Pd(PPh₃)4 / diethyl ether; various solvent(s) / 16 h

3.1: 87 percent / TBAF / tetrahydrofuran / 20 h / 20 °C

4.1: 86 percent / H₂ / Rh[(nbd)dppb]BF₄ / CH₂Cl₂ / 4 h / 36201.3 Torr

5.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 20 °C

6.1: 93 percent / DDQ / CH₂Cl₂ / 1 h / 20 °C / pH 7

7.1: triethylamine / CH₂Cl₂ / 1.5 h / 20 °C

8.1: HF / acetonitrile / 3 h / 20 °C

9.1: 98 percent / potassium carbonate / methanol / 0.75 h

10.1: 92 percent / lithium perchlorate / acetonitrile / 24 h / 70 °C

11.1: 81 percent / diisopropylethylamine / CH₂Cl₂ / 28 h / 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; hydrogen fluoride; tetrabutyl ammonium fluoride; hydrogen; iodine; tert.-butyl lithium; lithium perchlorate; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; zinc(II) chloride; {(1,4-bis(diphenylphosphino)butane)Rh(norbornadiene)}BF₄; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetonitrile; Petroleum ether; 2.2: Negishi coupling;

DOI:10.1021/ja028941u

upstream raw materials:

(+)-(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

5R-tert-butyldimethylsiloxy-2S,4S-dimethyl-6-benzyloxy-hexanol

Downstream raw materials:

C₂₇H₄₆O₆

C₂₇H₄₆O₇

3S,11R-bis-methoxymethoxy-4S,6S,8R,10S-tetramethyl-12-benzyloxy-dodecanoic acid methyl ester

borrelidin

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