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

Base Information

• Chemical Name: (2R,3S,4R,6S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-((S)-1-ethyl-allyloxy)-tetrahydro-pyran
• CAS No.: 688034-87-9
• Molecular Formula: C₃₂H₃₈O₅
• Molecular Weight: 502.651
• Mol file: 688034-87-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about (2R,3S,4R,6S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-((S)-1-ethyl-allyloxy)-tetrahydro-pyran 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:

3,4,6-tri-O-benzyl-D-glucal (55628-54-1) + 1-Penten-3-ol (616-25-1) → (2R,3S,4R,6S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-((S)-1-ethyl-allyloxy)-tetrahydro-pyran (688034-87-9) + (2R,3S,4R,6S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-((R)-1-ethyl-allyloxy)-tetrahydro-pyran (688034-86-8)

Guidance literature:

triphenylphosphine hydrobromide;

DOI:10.1016/j.tetlet.2004.01.151

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:

(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-Hydroxy-icosa-5,8,11,14-tetraenoic acid

Guidance literature:

Multi-step reaction with 3 steps

1.1: 9-BBN-H / tetrahydrofuran / 3 h / 23 °C

1.2: 92 percent / Cs₂CO₃ / Pd(dppf)Cl₂; Ph₃As / tetrahydrofuran; dimethylformamide; H₂O / 6 h / 23 °C

2.1: 91 percent / PTSA / methanol / 6 h / 65 °C

3.1: 94 percent / NaOH / tetrahydrofuran; H₂O / 6 h / 23 °C

With sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; water; 1.2: Suzuki-Miyaura cross-coupling;

DOI:10.1016/j.tetlet.2004.01.151

upstream raw materials:

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

1-Penten-3-ol

Downstream raw materials:

(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