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

Base Information

Chemical Name:4-{6-[10-(tert-butyl-diphenyl-silanyloxy)-6-hydroxy-11-methoxymethoxy-2-methyl-4-methylene-13-phenyl-trideca-7,12-dienyl]-5,6-dihydro-2H-pyran-2-yl}-but-2-enoic acid methyl ester
CAS No.:916771-68-1
Molecular Formula:C₄₉H₆₄O₇Si
Molecular Weight:793.128
Hs Code.:

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

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

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

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

There total 27 articles about 4-{6-[10-(tert-butyl-diphenyl-silanyloxy)-6-hydroxy-11-methoxymethoxy-2-methyl-4-methylene-13-phenyl-trideca-7,12-dienyl]-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:

: 916771-82-9
4-[6-(4-hydroxymethyl-2-methyl-pent-4-enyl)-5,6-dihydro-2H-pyran-2-yl]-but-2-enoic acid methyl ester

: 916771-68-1
4-{6-[10-(tert-butyl-diphenyl-silanyloxy)-6-hydroxy-11-methoxymethoxy-2-methyl-4-methylene-13-phenyl-trideca-7,12-dienyl]-5,6-dihydro-2H-pyran-2-yl}-but-2-enoic acid methyl ester

Guidance literature:: Multi-step reaction with 3 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

With dmap; triethylamine; scandium tris(trifluoromethanesulfonate); bis(dibenzylideneacetone)-palladium⁽⁰⁾; In dichloromethane; dimethyl sulfoxide;
DOI:10.1016/j.tetlet.2006.09.104

Reference yield:

: 916771-83-0
4-[6-(4-acetoxymethyl-2-methyl-pent-4-enyl)-5,6-dihydro-2H-pyran-2-yl]-but-2-enoic acid methyl ester

: 916771-68-1
4-{6-[10-(tert-butyl-diphenyl-silanyloxy)-6-hydroxy-11-methoxymethoxy-2-methyl-4-methylene-13-phenyl-trideca-7,12-dienyl]-5,6-dihydro-2H-pyran-2-yl}-but-2-enoic acid methyl ester

Guidance literature:: Multi-step reaction with 2 steps

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

2: Sc(OTf)3 / CH₂Cl₂ / -78 °C

With scandium tris(trifluoromethanesulfonate); bis(dibenzylideneacetone)-palladium⁽⁰⁾; In dichloromethane; dimethyl sulfoxide;
DOI:10.1016/j.tetlet.2006.09.104

Reference yield:

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

: 916771-68-1
4-{6-[10-(tert-butyl-diphenyl-silanyloxy)-6-hydroxy-11-methoxymethoxy-2-methyl-4-methylene-13-phenyl-trideca-7,12-dienyl]-5,6-dihydro-2H-pyran-2-yl}-but-2-enoic acid methyl ester

Guidance literature:: Multi-step reaction with 17 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

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; scandium tris(trifluoromethanesulfonate); 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