4-[6-(10-hydroxy-6,11-bis-methoxymethoxy-2-methyl-4-methylene-13-phenyl-trideca-7,12-dienyl)-5,6-dihydro-2H-pyran-2-yl]-but-2-enoic acid

Base Information

• Chemical Name: 4-[6-(10-hydroxy-6,11-bis-methoxymethoxy-2-methyl-4-methylene-13-phenyl-trideca-7,12-dienyl)-5,6-dihydro-2H-pyran-2-yl]-but-2-enoic acid
• CAS No.: 916771-54-5
• Molecular Formula: C₃₄H₄₈O₈
• Molecular Weight: 584.75
• Mol file: 916771-54-5.mol

Synonyms:4-[6-(10-hydroxy-6,11-bis-methoxymethoxy-2-methyl-4-methylene-13-phenyl-trideca-7,12-dienyl)-5,6-dihydro-2H-pyran-2-yl]-but-2-enoic acid

Chemical Property of 4-[6-(10-hydroxy-6,11-bis-methoxymethoxy-2-methyl-4-methylene-13-phenyl-trideca-7,12-dienyl)-5,6-dihydro-2H-pyran-2-yl]-but-2-enoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-[6-(10-hydroxy-6,11-bis-methoxymethoxy-2-methyl-4-methylene-13-phenyl-trideca-7,12-dienyl)-5,6-dihydro-2H-pyran-2-yl]-but-2-enoic acid

There total 33 articles about 4-[6-(10-hydroxy-6,11-bis-methoxymethoxy-2-methyl-4-methylene-13-phenyl-trideca-7,12-dienyl)-5,6-dihydro-2H-pyran-2-yl]-but-2-enoic acid 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: 79.0%

4-{6-[10-(tert-butyl-diphenyl-silanyloxy)-6,11-bis-methoxymethoxy-2-methyl-4-methylene-13-phenyl-trideca-7,12-dienyl]-5,6-dihydro-2H-pyran-2-yl}-but-2-enoic acid (916771-87-4) → 4-[6-(10-hydroxy-6,11-bis-methoxymethoxy-2-methyl-4-methylene-13-phenyl-trideca-7,12-dienyl)-5,6-dihydro-2H-pyran-2-yl]-but-2-enoic acid (916771-54-5)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃;

DOI:10.1016/j.tetlet.2006.09.104

Reference yield:

4-[6-(4-hydroxymethyl-2-methyl-pent-4-enyl)-5,6-dihydro-2H-pyran-2-yl]-but-2-enoic acid methyl ester (916771-82-9) → 4-[6-(10-hydroxy-6,11-bis-methoxymethoxy-2-methyl-4-methylene-13-phenyl-trideca-7,12-dienyl)-5,6-dihydro-2H-pyran-2-yl]-but-2-enoic acid (916771-54-5)

Guidance literature:

Multi-step reaction with 8 steps

1: 97 percent / DMAP; NEt₃ / CH₂Cl₂ / 0 °C

2: 74 percent / Pd(dba)2 / dimethylsulfoxide / 50 °C

3: Sc(OTf)3 / CH₂Cl₂ / -78 °C

4: 92 percent / i-Pr₂NEt / CH₂Cl₂ / 20 °C

5: 92 percent / DIBAH / toluene / -78 °C

6: 88 percent / MnO₂ / CH₂Cl₂ / 40 °C

7: 89 percent / NaClO₂; NaH₂PO₄; (CH₃)2C=CHCH₃ / 2-methyl-propan-2-ol; H₂O / 20 °C

8: 79 percent / TBAF / tetrahydrofuran / 20 °C

With dmap; manganese(IV) oxide; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; scandium tris(trifluoromethanesulfonate); bis(dibenzylideneacetone)-palladium⁽⁰⁾; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; toluene; tert-butyl alcohol;

DOI:10.1016/j.tetlet.2006.09.104

Reference yield:

4-[6-(4-acetoxymethyl-2-methyl-pent-4-enyl)-5,6-dihydro-2H-pyran-2-yl]-but-2-enoic acid methyl ester (916771-83-0) → 4-[6-(10-hydroxy-6,11-bis-methoxymethoxy-2-methyl-4-methylene-13-phenyl-trideca-7,12-dienyl)-5,6-dihydro-2H-pyran-2-yl]-but-2-enoic acid (916771-54-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 74 percent / Pd(dba)2 / dimethylsulfoxide / 50 °C

2: Sc(OTf)3 / CH₂Cl₂ / -78 °C

3: 92 percent / i-Pr₂NEt / CH₂Cl₂ / 20 °C

4: 92 percent / DIBAH / toluene / -78 °C

5: 88 percent / MnO₂ / CH₂Cl₂ / 40 °C

6: 89 percent / NaClO₂; NaH₂PO₄; (CH₃)2C=CHCH₃ / 2-methyl-propan-2-ol; H₂O / 20 °C

7: 79 percent / TBAF / tetrahydrofuran / 20 °C

With manganese(IV) oxide; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; scandium tris(trifluoromethanesulfonate); bis(dibenzylideneacetone)-palladium⁽⁰⁾; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; toluene; tert-butyl alcohol;

DOI:10.1016/j.tetlet.2006.09.104

upstream raw materials:

4-{6-[10-(tert-butyl-diphenyl-silanyloxy)-6,11-bis-methoxymethoxy-2-methyl-4-methylene-13-phenyl-trideca-7,12-dienyl]-5,6-dihydro-2H-pyran-2-yl}-but-2-enoic acid

1-oxiranyl-3-phenyl-prop-2-yn-1-ol

2-(1-methoxymethoxy-3-phenyl-prop-2-ynyl)-oxirane

1-chloro-5-phenyl-pent-4-yne-2,3-diol

Downstream raw materials:

11-methoxymethoxy-7-(1-methoxymethoxy-3-phenyl-allyl)-15-methyl-13-methylene-6,21-dioxa-bicyclo[15.3.1]heneicosa-3,9,19-trien-5-one