(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
Hs Code.:

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

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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

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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%

: 688034-83-5
methyl 15-bromopentadeca-5(Z),8(Z),11(Z),14(Z)-tetraenoate

: 688034-87-9
(2R,3S,4R,6S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-((S)-1-ethyl-allyloxy)-tetrahydro-pyran

: 688034-93-7
(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

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:

: 55628-54-1
3,4,6-tri-O-benzyl-D-glucal

: 688034-93-7
(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

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:

: 616-25-1
1-Penten-3-ol

: 688034-93-7
(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

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