(2S,3S,5Z,10S,11R)-2-benzyloxy-11,12-bis(tert-butyldimethylsilyloxy)-3-(2-methoxyethoxymethoxy)-10-methyldodec-5-ene

Base Information

• Chemical Name: (2S,3S,5Z,10S,11R)-2-benzyloxy-11,12-bis(tert-butyldimethylsilyloxy)-3-(2-methoxyethoxymethoxy)-10-methyldodec-5-ene
• CAS No.: 565194-18-5
• Molecular Formula: C₃₆H₆₈O₆Si₂
• Molecular Weight: 653.103
• Mol file: 565194-18-5.mol

Synonyms:(2S,3S,5Z,10S,11R)-2-benzyloxy-11,12-bis(tert-butyldimethylsilyloxy)-3-(2-methoxyethoxymethoxy)-10-methyldodec-5-ene

Chemical Property of (2S,3S,5Z,10S,11R)-2-benzyloxy-11,12-bis(tert-butyldimethylsilyloxy)-3-(2-methoxyethoxymethoxy)-10-methyldodec-5-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,5Z,10S,11R)-2-benzyloxy-11,12-bis(tert-butyldimethylsilyloxy)-3-(2-methoxyethoxymethoxy)-10-methyldodec-5-ene

There total 16 articles about (2S,3S,5Z,10S,11R)-2-benzyloxy-11,12-bis(tert-butyldimethylsilyloxy)-3-(2-methoxyethoxymethoxy)-10-methyldodec-5-ene 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,3R)-3,4-bis(tert-butyldimethylsilyloxy)-2-methylbutanal (565194-12-9) → (2S,3S,5Z,10S,11R)-2-benzyloxy-11,12-bis(tert-butyldimethylsilyloxy)-3-(2-methoxyethoxymethoxy)-10-methyldodec-5-ene (565194-18-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: NaHMDS / tetrahydrofuran / 0.33 h / 20 °C

1.2: 1.8 g / tetrahydrofuran / 2 h / 0 °C

2.1: 60 percent / H₂ / Pd/C / ethyl acetate / 6 h

3.1: 78 percent / I₂; Ph₃P; imidazole / CH₂Cl₂ / 8 h

4.1: xylene / 3 h / 150 °C

5.1: NaHMDS / tetrahydrofuran; hexamethylphosphoric acid triamide / 2 h / -78 °C

5.2: tetrahydrofuran / 15 h / -78 - 25 °C

With 1H-imidazole; hydrogen; iodine; sodium hexamethyldisilazane; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; ethyl acetate; xylene; 1.2: Wittig reaction / 5.2: Wittig reaction;

DOI:10.1039/b508001k

Reference yield:

(2R,3S)-1,2-bis(tert-butyldimethylsilyloxy)-3-methylpent-4-ene (565194-32-3) → (2S,3S,5Z,10S,11R)-2-benzyloxy-11,12-bis(tert-butyldimethylsilyloxy)-3-(2-methoxyethoxymethoxy)-10-methyldodec-5-ene (565194-18-5)

Guidance literature:

Multi-step reaction with 7 steps

1.1: aq. OsO₄; NMO / acetone / 6 h / 25 °C

2.1: 9.0 g / aq. NaIO₄ / acetone / 0.5 h / 25 °C

3.1: NaHMDS / tetrahydrofuran / 0.33 h / 20 °C

3.2: 1.8 g / tetrahydrofuran / 2 h / 0 °C

4.1: 60 percent / H₂ / Pd/C / ethyl acetate / 6 h

5.1: 78 percent / I₂; Ph₃P; imidazole / CH₂Cl₂ / 8 h

6.1: xylene / 3 h / 150 °C

7.1: NaHMDS / tetrahydrofuran; hexamethylphosphoric acid triamide / 2 h / -78 °C

7.2: tetrahydrofuran / 15 h / -78 - 25 °C

With 1H-imidazole; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; hydrogen; iodine; sodium hexamethyldisilazane; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; ethyl acetate; acetone; xylene; 3.2: Wittig reaction / 7.2: Wittig reaction;

DOI:10.1039/b508001k

Reference yield:

(2R,3S)-1-{[t-butyl(dimethyl)silyl]oxy}-3-methylpent-4-en-2-ol (565194-10-7) → (2S,3S,5Z,10S,11R)-2-benzyloxy-11,12-bis(tert-butyldimethylsilyloxy)-3-(2-methoxyethoxymethoxy)-10-methyldodec-5-ene (565194-18-5)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 89 percent / imidazole / dimethylformamide / 9 h / 25 °C

2.1: aq. OsO₄; NMO / acetone / 6 h / 25 °C

3.1: 9.0 g / aq. NaIO₄ / acetone / 0.5 h / 25 °C

4.1: NaHMDS / tetrahydrofuran / 0.33 h / 20 °C

4.2: 1.8 g / tetrahydrofuran / 2 h / 0 °C

5.1: 60 percent / H₂ / Pd/C / ethyl acetate / 6 h

6.1: 78 percent / I₂; Ph₃P; imidazole / CH₂Cl₂ / 8 h

7.1: xylene / 3 h / 150 °C

8.1: NaHMDS / tetrahydrofuran; hexamethylphosphoric acid triamide / 2 h / -78 °C

8.2: tetrahydrofuran / 15 h / -78 - 25 °C

With 1H-imidazole; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; hydrogen; iodine; sodium hexamethyldisilazane; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetone; xylene; 4.2: Wittig reaction / 8.2: Wittig reaction;

DOI:10.1039/b508001k

upstream raw materials:

(3S,4S)-4-benzyloxy-3-(2-methoxyethoxymethoxy)pentanal

benzyl bromide

tert-butyldimethylsilyl chloride

(2R,3S)-1-{[t-butyl(dimethyl)silyl]oxy}-3-methylpent-4-en-2-ol