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

Base Information

• Chemical Name: 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
• CAS No.: 916771-88-5
• Molecular Formula: C₃₄H₄₆O₇
• Molecular Weight: 566.735

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of 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

There total 34 articles about 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 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:

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) → 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 (916771-88-5)

Guidance literature:

Multi-step reaction with 9 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

9: 42 percent / 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; 9: Yamaguchi macrolactonization;

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) → 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 (916771-88-5)

Guidance literature:

Multi-step reaction with 8 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

8: 42 percent / 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; 8: Yamaguchi macrolactonization;

DOI:10.1016/j.tetlet.2006.09.104

Reference yield:

5-(tert-butyl-diphenyl-silanyloxymethyl)-3-methyl-hex-5-enal (916771-74-9) → 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 (916771-88-5)

Guidance literature:

Multi-step reaction with 23 steps

1: LDA / tetrahydrofuran / -100 °C

2: 98 percent / imidazole / CH₂Cl₂ / 20 °C

3: 92 percent / DIBAH / tetrahydrofuran / -78 °C

4: 99 percent / 0 °C

5: LDA / tetrahydrofuran / 4 h / -100 °C

6: 99 percent / TFA / H₂O / 0.83 h / 20 °C

7: NaOH / methanol / 1.33 h / 20 °C

8: p-TsOH / CH₂Cl₂ / 1.42 h / 20 °C

9: 97 percent / NEt₃; MsCl / CH₂Cl₂ / 0 °C

10: DIBAH / toluene / -78 °C

11: CSA / 20 °C

12: 75 percent / LiClO₄ / ethyl acetate / 20 °C

13: -78 °C

14: 97 percent / HF; pyridine / acetonitrile / 20 °C

15: 97 percent / DMAP; NEt₃ / CH₂Cl₂ / 0 °C

16: 74 percent / Pd(dba)2 / dimethylsulfoxide / 50 °C

17: Sc(OTf)3 / CH₂Cl₂ / -78 °C

18: 92 percent / i-Pr₂NEt / CH₂Cl₂ / 20 °C

19: 92 percent / DIBAH / toluene / -78 °C

20: 88 percent / MnO₂ / CH₂Cl₂ / 40 °C

21: 89 percent / NaClO₂; NaH₂PO₄; (CH₃)2C=CHCH₃ / 2-methyl-propan-2-ol; H₂O / 20 °C

22: 79 percent / TBAF / tetrahydrofuran / 20 °C

23: 42 percent / 20 °C

With pyridine; 1H-imidazole; dmap; manganese(IV) oxide; sodium hydroxide; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; camphor-10-sulfonic acid; hydrogen fluoride; tetrabutyl ammonium fluoride; lithium perchlorate; diisobutylaluminium hydride; toluene-4-sulfonic acid; methanesulfonyl chloride; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; scandium tris(trifluoromethanesulfonate); lithium diisopropyl amide; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; toluene; acetonitrile; tert-butyl alcohol; 4: Dess-Martin oxidation / 12: Mulzer's enol ether method / 13: Still-Gennari reaction / 23: Yamaguchi macrolactonization;

DOI:10.1016/j.tetlet.2006.09.104

upstream raw materials:

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

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

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