4-{6-[2-methyl-4-(1,10,10-trimethyl-6-phenyl-3,5-dioxa-4-bora-tricyclo[5.2.1.0^2,6]dec-4-ylmethyl)-pent-4-enyl]-5,6-dihydro-2H-pyran-2-yl}-but-2-enoic acid methyl ester

Base Information

• Chemical Name: 4-{6-[2-methyl-4-(1,10,10-trimethyl-6-phenyl-3,5-dioxa-4-bora-tricyclo[5.2.1.0^2,6]dec-4-ylmethyl)-pent-4-enyl]-5,6-dihydro-2H-pyran-2-yl}-but-2-enoic acid methyl ester
• CAS No.: 916771-56-7
• Molecular Formula: C₃₃H₄₅BO₅
• Molecular Weight: 532.528

Synonyms:4-{6-[2-methyl-4-(1,10,10-trimethyl-6-phenyl-3,5-dioxa-4-bora-tricyclo[5.2.1.0^2,6]dec-4-ylmethyl)-pent-4-enyl]-5,6-dihydro-2H-pyran-2-yl}-but-2-enoic acid methyl ester

Chemical Property of 4-{6-[2-methyl-4-(1,10,10-trimethyl-6-phenyl-3,5-dioxa-4-bora-tricyclo[5.2.1.0^2,6]dec-4-ylmethyl)-pent-4-enyl]-5,6-dihydro-2H-pyran-2-yl}-but-2-enoic acid methyl ester

Chemical Property:

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Technology Process of 4-{6-[2-methyl-4-(1,10,10-trimethyl-6-phenyl-3,5-dioxa-4-bora-tricyclo[5.2.1.0^2,6]dec-4-ylmethyl)-pent-4-enyl]-5,6-dihydro-2H-pyran-2-yl}-but-2-enoic acid methyl ester

There total 17 articles about 4-{6-[2-methyl-4-(1,10,10-trimethyl-6-phenyl-3,5-dioxa-4-bora-tricyclo[5.2.1.0^2,6]dec-4-ylmethyl)-pent-4-enyl]-5,6-dihydro-2H-pyran-2-yl}-but-2-enoic 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: 74.0%

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) + (3aS,3′aS,4S,4'S,7R,7′R,7aS,7′aS)-dodecahydro-7,7′,8,8,8′,8′-hexamethyl-3a,3′a-diphenyl-2,2′-bi-4,7-methanol-1,3,2-benzodioxaborole → 4-{6-[2-methyl-4-(1,10,10-trimethyl-6-phenyl-3,5-dioxa-4-bora-tricyclo[5.2.1.02,6]dec-4-ylmethyl)-pent-4-enyl]-5,6-dihydro-2H-pyran-2-yl}-but-2-enoic acid methyl ester (916771-56-7)

Guidance literature:

bis(dibenzylideneacetone)-palladium⁽⁰⁾; In dimethyl sulfoxide; at 50 ℃;

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-[2-methyl-4-(1,10,10-trimethyl-6-phenyl-3,5-dioxa-4-bora-tricyclo[5.2.1.02,6]dec-4-ylmethyl)-pent-4-enyl]-5,6-dihydro-2H-pyran-2-yl}-but-2-enoic acid methyl ester (916771-56-7)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With dmap; triethylamine; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In dichloromethane; dimethyl sulfoxide;

DOI:10.1016/j.tetlet.2006.09.104

Reference yield:

5-(tert-butyl-diphenyl-silanyloxymethyl)-3-methyl-hex-5-enal (916771-74-9) → 4-{6-[2-methyl-4-(1,10,10-trimethyl-6-phenyl-3,5-dioxa-4-bora-tricyclo[5.2.1.02,6]dec-4-ylmethyl)-pent-4-enyl]-5,6-dihydro-2H-pyran-2-yl}-but-2-enoic acid methyl ester (916771-56-7)

Guidance literature:

Multi-step reaction with 16 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

With pyridine; 1H-imidazole; dmap; sodium hydroxide; camphor-10-sulfonic acid; hydrogen fluoride; lithium perchlorate; diisobutylaluminium hydride; toluene-4-sulfonic acid; methanesulfonyl chloride; triethylamine; trifluoroacetic acid; lithium diisopropyl amide; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; toluene; acetonitrile; 4: Dess-Martin oxidation / 12: Mulzer's enol ether method / 13: Still-Gennari reaction;

DOI:10.1016/j.tetlet.2006.09.104

upstream raw materials:

4-[6-(4-acetoxymethyl-2-methyl-pent-4-enyl)-5,6-dihydro-2H-pyran-2-yl]-but-2-enoic acid methyl ester

4-[6-(4-hydroxymethyl-2-methyl-pent-4-enyl)-5,6-dihydro-2H-pyran-2-yl]-but-2-enoic acid methyl ester

5-(tert-butyl-diphenyl-silanyloxymethyl)-3-methyl-hex-5-enal

6-[4-(tert-butyl-diphenyl-silanyloxymethyl)-2-methyl-pent-4-enyl]-5,6-dihydro-pyran-2-one

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

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

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-enal

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-en-1-ol

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