(2S,3S,5Z,10S)-2-benzyloxy-11-tert-butyldimethylsilyloxy-3-(2-methoxyethoxymethoxy)undec-5-ene

Base Information

• Chemical Name: (2S,3S,5Z,10S)-2-benzyloxy-11-tert-butyldimethylsilyloxy-3-(2-methoxyethoxymethoxy)undec-5-ene
• CAS No.: 565193-96-6
• Molecular Formula: C₂₉H₅₂O₅Si
• Molecular Weight: 508.814
• Mol file: 565193-96-6.mol

Synonyms:

Chemical Property of (2S,3S,5Z,10S)-2-benzyloxy-11-tert-butyldimethylsilyloxy-3-(2-methoxyethoxymethoxy)undec-5-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,5Z,10S)-2-benzyloxy-11-tert-butyldimethylsilyloxy-3-(2-methoxyethoxymethoxy)undec-5-ene

There total 15 articles about (2S,3S,5Z,10S)-2-benzyloxy-11-tert-butyldimethylsilyloxy-3-(2-methoxyethoxymethoxy)undec-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:

[(S)-6-(tert-Butyl-dimethyl-silanyloxy)-5-methyl-hexyl]-triphenyl-phosphonium; iodide + (3S,4S)-4-benzyloxy-3-(2-methoxyethoxymethoxy)pentanal (565193-84-2) → (2S,3S,5E,10S)-2-benzyloxy-11-tert-butyldimethylsilyloxy-3-(2-methoxyethoxymethoxy)undec-5-ene + (2S,3S,5Z,10S)-2-benzyloxy-11-tert-butyldimethylsilyloxy-3-(2-methoxyethoxymethoxy)undec-5-ene (565193-96-6)

Guidance literature:

[(S)-6-(tert-Butyl-dimethyl-silanyloxy)-5-methyl-hexyl]-triphenyl-phosphonium; iodide; With sodium hexamethyldisilazane; In tetrahydrofuran; at 0 ℃; for 0.25h;

(3S,4S)-4-benzyloxy-3-(2-methoxyethoxymethoxy)pentanal; In tetrahydrofuran; at 0 ℃;

DOI:10.1039/b508001k

Reference yield:

(S)-3-(tert-butyldimethylsilyloxy)-2-methylpropan-1-ol (105859-45-8) → (2S,3S,5Z,10S)-2-benzyloxy-11-tert-butyldimethylsilyloxy-3-(2-methoxyethoxymethoxy)undec-5-ene (565193-96-6)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 87 percent / I₂; Ph₃P; imidazole / CH₂Cl₂ / 8 h

2.1: 50 percent / Li₂CuCl₄ / tetrahydrofuran; CH₂Cl₂ / 4 h / -78 °C

3.1: BH₃*Me₂S / diethyl ether / 20 °C

3.2: 40 percent / NaOH; aq. H₂O₂ / 10 h / 25 °C

4.1: 80 percent / I₂; PPh₃; imidazole / CH₂Cl₂ / 8 h

5.1: 91 percent / 2 h / 100 °C

6.1: NaHMDS / tetrahydrofuran / 0.25 h / 0 °C

6.2: tetrahydrofuran / 0 °C

With 1H-imidazole; dilithium tetrachlorocuprate; dimethylsulfide borane complex; iodine; sodium hexamethyldisilazane; triphenylphosphine; In tetrahydrofuran; diethyl ether; dichloromethane; 6.2: Wittig reaction;

DOI:10.1039/b508001k

Reference yield:

methyl (R)-2-methyl-3-[(tert-butyldimethylsilyl)oxy]propionate (105859-44-7) → (2S,3S,5Z,10S)-2-benzyloxy-11-tert-butyldimethylsilyloxy-3-(2-methoxyethoxymethoxy)undec-5-ene (565193-96-6)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 78 percent / BH₃*Me₂S; Et₃N / methanol; tetrahydrofuran / 25 °C

2.1: 87 percent / I₂; Ph₃P; imidazole / CH₂Cl₂ / 8 h

3.1: 50 percent / Li₂CuCl₄ / tetrahydrofuran; CH₂Cl₂ / 4 h / -78 °C

4.1: BH₃*Me₂S / diethyl ether / 20 °C

4.2: 40 percent / NaOH; aq. H₂O₂ / 10 h / 25 °C

5.1: 80 percent / I₂; PPh₃; imidazole / CH₂Cl₂ / 8 h

6.1: 91 percent / 2 h / 100 °C

7.1: NaHMDS / tetrahydrofuran / 0.25 h / 0 °C

7.2: tetrahydrofuran / 0 °C

With 1H-imidazole; dilithium tetrachlorocuprate; dimethylsulfide borane complex; iodine; sodium hexamethyldisilazane; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 7.2: Wittig reaction;

DOI:10.1039/b508001k

upstream raw materials:

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

(S)-3-(tert-butyldimethylsilyloxy)-2-methylpropan-1-ol

methyl (R)-2-methyl-3-[(tert-butyldimethylsilyl)oxy]propionate

benzyl bromide