(S,E)-ethyl-6-(tert-butyldiphenylsilyloxy)-4-((tert-butyldiphenylsilyloxy)methyl)-2-methylhex-2-enoate

Base Information

• Chemical Name: (S,E)-ethyl-6-(tert-butyldiphenylsilyloxy)-4-((tert-butyldiphenylsilyloxy)methyl)-2-methylhex-2-enoate
• CAS No.: 1417795-80-2
• Molecular Formula: C₄₂H₅₄O₄Si₂
• Molecular Weight: 679.059

Synonyms:(S,E)-ethyl-6-(tert-butyldiphenylsilyloxy)-4-((tert-butyldiphenylsilyloxy)methyl)-2-methylhex-2-enoate

Chemical Property of (S,E)-ethyl-6-(tert-butyldiphenylsilyloxy)-4-((tert-butyldiphenylsilyloxy)methyl)-2-methylhex-2-enoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S,E)-ethyl-6-(tert-butyldiphenylsilyloxy)-4-((tert-butyldiphenylsilyloxy)methyl)-2-methylhex-2-enoate

There total 9 articles about (S,E)-ethyl-6-(tert-butyldiphenylsilyloxy)-4-((tert-butyldiphenylsilyloxy)methyl)-2-methylhex-2-enoate 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: 84.0%

(R)-4-(tert-butyldiphenylsilyloxy)-2-((tert-butyldiphenylsilyloxy)methyl)butanal (1417795-79-9) + (carbethoxyethylidene)triphenylphosphorane (21382-82-1) → (S,E)-ethyl-6-(tert-butyldiphenylsilyloxy)-4-((tert-butyldiphenylsilyloxy)methyl)-2-methylhex-2-enoate (1417795-80-2)

Guidance literature:

In dichloromethane; at 0 - 20 ℃; for 24.5h; Inert atmosphere;

DOI:10.1016/j.tet.2012.11.051

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → (S,E)-ethyl-6-(tert-butyldiphenylsilyloxy)-4-((tert-butyldiphenylsilyloxy)methyl)-2-methylhex-2-enoate (1417795-80-2)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 1H-imidazole; dmap / tetrahydrofuran / 24 h / 0 - 20 °C

2.1: 1H-imidazole; triphenylphosphine; iodine / tetrahydrofuran / 2 h / -20 - 20 °C

3.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C

3.2: 12 h / Reflux

4.1: lithium aluminium tetrahydride / diethyl ether / 1 h / 0 °C

5.1: lipase PS-D immobilized on diatomite / di-isopropyl ether / 20 °C / Molecular sieve; Inert atmosphere; Enzymatic reaction

6.1: 1H-imidazole; dmap / dichloromethane / 3 h / 0 - 20 °C

7.1: potassium carbonate; methanol / 20 °C

8.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.83 h / -78 °C

8.2: -78 - 20 °C

9.1: dichloromethane / 24.5 h / 0 - 20 °C / Inert atmosphere

With 1H-imidazole; methanol; dmap; lithium aluminium tetrahydride; oxalyl dichloride; lipase PS-D immobilized on diatomite; iodine; sodium hydride; potassium carbonate; dimethyl sulfoxide; triphenylphosphine; In tetrahydrofuran; diethyl ether; dichloromethane; di-isopropyl ether; mineral oil; 8.1: |Swern Oxidation / 9.1: |Wittig Olefination;

DOI:10.1016/j.tet.2012.11.051

Reference yield:

2-[(tert-butyldiphenylsilyl)oxy]ethanol (138499-16-8) → (S,E)-ethyl-6-(tert-butyldiphenylsilyloxy)-4-((tert-butyldiphenylsilyloxy)methyl)-2-methylhex-2-enoate (1417795-80-2)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 1H-imidazole; triphenylphosphine; iodine / tetrahydrofuran / 2 h / -20 - 20 °C

2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C

2.2: 12 h / Reflux

3.1: lithium aluminium tetrahydride / diethyl ether / 1 h / 0 °C

4.1: lipase PS-D immobilized on diatomite / di-isopropyl ether / 20 °C / Molecular sieve; Inert atmosphere; Enzymatic reaction

5.1: 1H-imidazole; dmap / dichloromethane / 3 h / 0 - 20 °C

6.1: potassium carbonate; methanol / 20 °C

7.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.83 h / -78 °C

7.2: -78 - 20 °C

8.1: dichloromethane / 24.5 h / 0 - 20 °C / Inert atmosphere

With 1H-imidazole; methanol; dmap; lithium aluminium tetrahydride; oxalyl dichloride; lipase PS-D immobilized on diatomite; iodine; sodium hydride; potassium carbonate; dimethyl sulfoxide; triphenylphosphine; In tetrahydrofuran; diethyl ether; dichloromethane; di-isopropyl ether; mineral oil; 7.1: |Swern Oxidation / 8.1: |Wittig Olefination;

DOI:10.1016/j.tet.2012.11.051

upstream raw materials:

2-[(tert-butyldiphenylsilyl)oxy]ethanol

tert-butylchlorodiphenylsilane

(R)-4-(tert-butyldiphenylsilyloxy)-2-((tert-butyldiphenylsilyloxy)methyl)butanal

(carbethoxyethylidene)triphenylphosphorane

Downstream raw materials:

(2E,4E,6S)-(2R,3R)-2-((2S,4R)-5-(4-methoxybenzyloxy)-4-methylpentan-2-yl)-3,6-dihydro-6-oxo-2H-pyran-3-yl 8-tert-butyldiphenylsilyloxy-6-(tert-butyldiphenylsilyloxy-methyl)-4-methylocta-2,4-dienoate

(2E,4E,6S)-(2R,3R)-3,6-dihydro-2-((2S,4R)-5-iodo-4-methylpentan-2-yl)-6-oxo-2H-pyran-3-yl 8-tert-butyldiphenylsilyloxy-6-(tert-butyldiphenylsilyloxy-methyl)-4-methylocta-2,4-dienoate

(2E,4E,6S)-(2R,3R)-3,6-dihydro-2-((E,2S,4R)-4,6-dimethyloct-6-en-2-yl)-6-oxo-2H-pyran-3-yl 8-tert-butyldiphenylsilyloxy-6-(tert-butyldiphenylsilyloxy-methyl)-4-methylocta-2,4-dienoate

(-)-(S,2E,4E)-((2R,3R)-2-((2S,4R,E)-4,6-dimethyloct-6-en-2-yl)-6-oxo-3,6-dihydro-2H-pyran-3-yl) 8-hydroxy-6-(hydroxymethyl)-4-methylocta-2,4-dienoate

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