2,2-di(hydroxymethyl)propyl 12S-(t-butyldiphenylsilyloxy)eicosa-5Z,8Z,10E,14Z-tetraenoate

Base Information

• Chemical Name: 2,2-di(hydroxymethyl)propyl 12S-(t-butyldiphenylsilyloxy)eicosa-5Z,8Z,10E,14Z-tetraenoate
• CAS No.: 131393-04-9
• Molecular Formula: C₄₁H₆₀O₅Si
• Molecular Weight: 661.01
• Mol file: 131393-04-9.mol

Synonyms:2,2-di(hydroxymethyl)propyl 12S-(t-butyldiphenylsilyloxy)eicosa-5Z,8Z,10E,14Z-tetraenoate

Chemical Property of 2,2-di(hydroxymethyl)propyl 12S-(t-butyldiphenylsilyloxy)eicosa-5Z,8Z,10E,14Z-tetraenoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,2-di(hydroxymethyl)propyl 12S-(t-butyldiphenylsilyloxy)eicosa-5Z,8Z,10E,14Z-tetraenoate

There total 16 articles about 2,2-di(hydroxymethyl)propyl 12S-(t-butyldiphenylsilyloxy)eicosa-5Z,8Z,10E,14Z-tetraenoate 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: 68.0%

1-(4-methyl-2,6,7-trioxabicyclo<2.2.2>octyl)-11S-(t-butyldiphenylsilyloxy)nonadeca-4Z,7Z,9E,13Z-tetraene (131393-03-8) → 2,2-di(hydroxymethyl)propyl 12S-(t-butyldiphenylsilyloxy)eicosa-5Z,8Z,10E,14Z-tetraenoate (131393-04-9)

Guidance literature:

With oxalic acid; In tetrahydrofuran; for 1h; Ambient temperature;

Reference yield:

1-(3-bromopropyl)-4-methyl-2,6,7-trioxabicyclo[2,2,2]octane (89276-36-8) → 2,2-di(hydroxymethyl)propyl 12S-(t-butyldiphenylsilyloxy)eicosa-5Z,8Z,10E,14Z-tetraenoate (131393-04-9)

Guidance literature:

Multi-step reaction with 8 steps

1: 81 percent / tetrahydrofuran; dimethylformamide; paraffin; xylene / 20 h / 1. -80 deg C to -75 deg C, 90 min, 2. to room temperature, 2 h 3. room temperature

2: 1. n-butyllithium / 1. DME, hexane, -78 deg C, 75 min 2. 10 deg C, 23 h

3: 92 percent / H₂ / NaBH₄, Ni(Ac)2*4H₂O, ethylene diamine / ethanol / 2 h

4: 73 percent / NEt₃ / diethyl ether / 0 °C

5: 86 percent / NaI, K₂CO₃ / acetone / 168 h / 35 °C

6: 76 percent / K₂CO₃ / acetonitrile / 72 h / 45 °C

7: 1. n-butyllithium / 1. -20 deg C, THF, hexane 2. a. -80 deg C, b. warm up to -10 deg C, 75 min c. 90 min, -10 deg C

8: 68 percent / aq. oxalic acid / tetrahydrofuran / 1 h / Ambient temperature

With n-butyllithium; hydrogen; oxalic acid; potassium carbonate; triethylamine; sodium iodide; sodium tetrahydroborate; nickel diacetate; ethylenediamine; In tetrahydrofuran; diethyl ether; ethanol; N,N-dimethyl-formamide; acetone; acetonitrile; paraffin; xylene;

Reference yield:

(3-methyl-3-oxetanyl)methyl 4-bromobutanoate (89276-32-4) → 2,2-di(hydroxymethyl)propyl 12S-(t-butyldiphenylsilyloxy)eicosa-5Z,8Z,10E,14Z-tetraenoate (131393-04-9)

Guidance literature:

Multi-step reaction with 9 steps

1: 80 percent / BF₃*Et₂O / CH₂Cl₂ / 1. -10 deg C to 0 deg C, 2 h 2. 0 deg C, 7 h

2: 81 percent / tetrahydrofuran; dimethylformamide; paraffin; xylene / 20 h / 1. -80 deg C to -75 deg C, 90 min, 2. to room temperature, 2 h 3. room temperature

3: 1. n-butyllithium / 1. DME, hexane, -78 deg C, 75 min 2. 10 deg C, 23 h

4: 92 percent / H₂ / NaBH₄, Ni(Ac)2*4H₂O, ethylene diamine / ethanol / 2 h

5: 73 percent / NEt₃ / diethyl ether / 0 °C

6: 86 percent / NaI, K₂CO₃ / acetone / 168 h / 35 °C

7: 76 percent / K₂CO₃ / acetonitrile / 72 h / 45 °C

8: 1. n-butyllithium / 1. -20 deg C, THF, hexane 2. a. -80 deg C, b. warm up to -10 deg C, 75 min c. 90 min, -10 deg C

9: 68 percent / aq. oxalic acid / tetrahydrofuran / 1 h / Ambient temperature

With n-butyllithium; hydrogen; oxalic acid; potassium carbonate; triethylamine; sodium iodide; sodium tetrahydroborate; boron trifluoride diethyl etherate; nickel diacetate; ethylenediamine; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; acetone; acetonitrile; paraffin; xylene;

upstream raw materials:

1-(4-methyl-2,6,7-trioxabicyclo<2.2.2>octyl)-11S-(t-butyldiphenylsilyloxy)nonadeca-4Z,7Z,9E,13Z-tetraene

(2S)-1,2-dihydroxydec-4Z-ene

1-(3-bromopropyl)-4-methyl-2,6,7-trioxabicyclo[2,2,2]octane

(3-methyl-3-oxetanyl)methyl 4-bromobutanoate

Downstream raw materials:

12-hydroxyeicosatetraenoic acid

methyl 12(S)-<(tert-butyldiphenylsilyl)oxy>-5(Z),8(Z),10(E),14(Z)-eicosatetraenoate