(5Z,8Z,11Z,14Z)-(S)-18-((2S,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-icosa-5,8,11,14-tetraenoic acid methyl ester

Base Information

• Chemical Name: (5Z,8Z,11Z,14Z)-(S)-18-((2S,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-icosa-5,8,11,14-tetraenoic acid methyl ester
• CAS No.: 688034-93-7
• Molecular Formula: C₄₈H₆₂O₇
• Molecular Weight: 751.016
• Mol file: 688034-93-7.mol

Synonyms:(5Z,8Z,11Z,14Z)-(S)-18-((2S,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-icosa-5,8,11,14-tetraenoic acid methyl ester

Chemical Property of (5Z,8Z,11Z,14Z)-(S)-18-((2S,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-icosa-5,8,11,14-tetraenoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5Z,8Z,11Z,14Z)-(S)-18-((2S,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-icosa-5,8,11,14-tetraenoic acid methyl ester

There total 5 articles about (5Z,8Z,11Z,14Z)-(S)-18-((2S,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-icosa-5,8,11,14-tetraenoic acid methyl ester 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: 92.0%

methyl 15-bromopentadeca-5(Z),8(Z),11(Z),14(Z)-tetraenoate (688034-83-5) + (2R,3S,4R,6S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-((S)-1-ethyl-allyloxy)-tetrahydro-pyran (688034-87-9) → (5Z,8Z,11Z,14Z)-(S)-18-((2S,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-icosa-5,8,11,14-tetraenoic acid methyl ester (688034-93-7)

Guidance literature:

methyl 15-bromopentadeca-5(Z),8(Z),11(Z),14(Z)-tetraenoate; (2R,3S,4R,6S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-((S)-1-ethyl-allyloxy)-tetrahydro-pyran; With 9-borabicyclo[3.3.1]nonane dimer; In tetrahydrofuran; at 23 ℃; for 3h;

With caesium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; triphenyl-arsane; In tetrahydrofuran; water; N,N-dimethyl-formamide; at 23 ℃; for 6h; Further stages.;

DOI:10.1016/j.tetlet.2004.01.151

Reference yield:

3,4,6-tri-O-benzyl-D-glucal (55628-54-1) → (5Z,8Z,11Z,14Z)-(S)-18-((2S,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-icosa-5,8,11,14-tetraenoic acid methyl ester (688034-93-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: HBr*PPh₃

2.1: 9-BBN-H / tetrahydrofuran / 3 h / 23 °C

2.2: 92 percent / Cs₂CO₃ / Pd(dppf)Cl₂; Ph₃As / tetrahydrofuran; dimethylformamide; H₂O / 6 h / 23 °C

With 9-borabicyclo[3.3.1]nonane dimer; triphenylphosphine hydrobromide; In tetrahydrofuran; 2.2: Suzuki-Miyaura cross-coupling;

DOI:10.1016/j.tetlet.2004.01.151

Reference yield:

1-Penten-3-ol (616-25-1) → (5Z,8Z,11Z,14Z)-(S)-18-((2S,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-icosa-5,8,11,14-tetraenoic acid methyl ester (688034-93-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: HBr*PPh₃

2.1: 9-BBN-H / tetrahydrofuran / 3 h / 23 °C

2.2: 92 percent / Cs₂CO₃ / Pd(dppf)Cl₂; Ph₃As / tetrahydrofuran; dimethylformamide; H₂O / 6 h / 23 °C

With 9-borabicyclo[3.3.1]nonane dimer; triphenylphosphine hydrobromide; In tetrahydrofuran; 2.2: Suzuki-Miyaura cross-coupling;

DOI:10.1016/j.tetlet.2004.01.151

upstream raw materials:

methyl 15-bromopentadeca-5(Z),8(Z),11(Z),14(Z)-tetraenoate

(2R,3S,4R,6S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-((S)-1-ethyl-allyloxy)-tetrahydro-pyran

3,4,6-tri-O-benzyl-D-glucal

1-Penten-3-ol