(E)-(1S,4R,5R)-1-((E)-(S)-4-allyloxy-1-ethylbut-2-enyl)-7-( tert-butyldiphenylsilanyloxy)-4-hydroxy-5-methoxymethoxy-4-(2-trityloxyethyl)hept-2-en-1-yl acrylate

Base Information

• Chemical Name: (E)-(1S,4R,5R)-1-((E)-(S)-4-allyloxy-1-ethylbut-2-enyl)-7-( tert-butyldiphenylsilanyloxy)-4-hydroxy-5-methoxymethoxy-4-(2-trityloxyethyl)hept-2-en-1-yl acrylate
• CAS No.: 1120309-21-8
• Molecular Formula: C₅₈H₇₀O₈Si
• Molecular Weight: 923.274

Synonyms:(E)-(1S,4R,5R)-1-((E)-(S)-4-allyloxy-1-ethylbut-2-enyl)-7-( tert-butyldiphenylsilanyloxy)-4-hydroxy-5-methoxymethoxy-4-(2-trityloxyethyl)hept-2-en-1-yl acrylate

Chemical Property of (E)-(1S,4R,5R)-1-((E)-(S)-4-allyloxy-1-ethylbut-2-enyl)-7-( tert-butyldiphenylsilanyloxy)-4-hydroxy-5-methoxymethoxy-4-(2-trityloxyethyl)hept-2-en-1-yl acrylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(1S,4R,5R)-1-((E)-(S)-4-allyloxy-1-ethylbut-2-enyl)-7-( tert-butyldiphenylsilanyloxy)-4-hydroxy-5-methoxymethoxy-4-(2-trityloxyethyl)hept-2-en-1-yl acrylate

There total 15 articles about (E)-(1S,4R,5R)-1-((E)-(S)-4-allyloxy-1-ethylbut-2-enyl)-7-( tert-butyldiphenylsilanyloxy)-4-hydroxy-5-methoxymethoxy-4-(2-trityloxyethyl)hept-2-en-1-yl acrylate 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: 100.0%

(5E,9E)-(3R,4R,7S,8S)-11-allyloxy-1-(tert-butyldiphenylsilanyloxy)-8-ethyl-3-methoxymethoxy-4-(2-trityloxyethyl)-undeca-5,9-diene-4,7-diol (1120309-38-7) + acryloyl chloride (814-68-6,25189-84-8) → (E)-(1S,4R,5R)-1-((E)-(S)-4-allyloxy-1-ethylbut-2-enyl)-7-( tert-butyldiphenylsilanyloxy)-4-hydroxy-5-methoxymethoxy-4-(2-trityloxyethyl)hept-2-en-1-yl acrylate (1120309-21-8)

Guidance literature:

With dmap; N-ethyl-N,N-diisopropylamine; In dichloromethane; at -78 ℃; for 2h;

DOI:10.1016/j.tet.2010.05.050

Reference yield:

2-(allyloxy)-N-methoxy-N-methylacetamide (1120309-29-6) → (E)-(1S,4R,5R)-1-((E)-(S)-4-allyloxy-1-ethylbut-2-enyl)-7-( tert-butyldiphenylsilanyloxy)-4-hydroxy-5-methoxymethoxy-4-(2-trityloxyethyl)hept-2-en-1-yl acrylate (1120309-21-8)

Guidance literature:

Multi-step reaction with 9 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.67 h / -78 - 0 °C

1.2: -78 - -40 °C

2.1: (1S,2S)-(+)-N-tosyl-1,2-diphenylethane-1,2-diamine[η6-1-isopropyl-4-methylbenzene]-ruthenium(II); isopropyl alcohol / 0.75 h / 20 °C

3.1: copper(I) bromide; lithium bromide; zinc / tetrahydrofuran; ethylene dibromide; isopropyl alcohol / 18 h / 20 °C / Reflux

4.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 0 °C

5.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C

6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C

7.1: isopropylmagnesium chloride / tetrahydrofuran; diethyl ether / -20 - 0 °C

7.2: 1.5 h / -20 °C

8.1: sodium bis(2-methoxyethoxy)aluminium dihydride / diethyl ether; toluene / 6 h / 0 °C

9.1: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / -78 °C

9.2: 2 h / -78 °C

With dmap; (1S,2S)-(+)-N-tosyl-1,2-diphenylethane-1,2-diamine[η6-1-isopropyl-4-methylbenzene]-ruthenium(II); n-butyllithium; potassium tert-butylate; tetrabutyl ammonium fluoride; isopropylmagnesium chloride; N-ethyl-N,N-diisopropylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; isopropyl alcohol; copper(I) bromide; lithium bromide; zinc; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; ethylene dibromide; isopropyl alcohol; toluene; 5.1: [2,3]-Wittig rearrangement;

DOI:10.1021/ol8029142

Reference yield:

2-(allyloxy)acetic acid (22577-14-6) → (E)-(1S,4R,5R)-1-((E)-(S)-4-allyloxy-1-ethylbut-2-enyl)-7-( tert-butyldiphenylsilanyloxy)-4-hydroxy-5-methoxymethoxy-4-(2-trityloxyethyl)hept-2-en-1-yl acrylate (1120309-21-8)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 4-methyl-morpholine; isobutyl chloroformate / dichloromethane / 1.5 h / -15 °C

1.2: 16.25 h / 0.2 °C

2.1: n-butyllithium / tetrahydrofuran; hexane / 0.67 h / -78 - 0 °C

2.2: -78 - -40 °C

3.1: (1S,2S)-(+)-N-tosyl-1,2-diphenylethane-1,2-diamine[η6-1-isopropyl-4-methylbenzene]-ruthenium(II); isopropyl alcohol / 0.75 h / 20 °C

4.1: copper(I) bromide; lithium bromide; zinc / tetrahydrofuran; ethylene dibromide; isopropyl alcohol / 18 h / 20 °C / Reflux

5.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 0 °C

6.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C

7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C

8.1: isopropylmagnesium chloride / tetrahydrofuran; diethyl ether / -20 - 0 °C

8.2: 1.5 h / -20 °C

9.1: sodium bis(2-methoxyethoxy)aluminium dihydride / diethyl ether; toluene / 6 h / 0 °C

10.1: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / -78 °C

10.2: 2 h / -78 °C

With 4-methyl-morpholine; dmap; (1S,2S)-(+)-N-tosyl-1,2-diphenylethane-1,2-diamine[η6-1-isopropyl-4-methylbenzene]-ruthenium(II); n-butyllithium; potassium tert-butylate; tetrabutyl ammonium fluoride; isopropylmagnesium chloride; N-ethyl-N,N-diisopropylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; isopropyl alcohol; copper(I) bromide; lithium bromide; zinc; isobutyl chloroformate; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; ethylene dibromide; isopropyl alcohol; toluene; 6.1: [2,3]-Wittig rearrangement;

DOI:10.1021/ol8029142

upstream raw materials:

(5E,9E)-(3R,4R,7S,8S)-11-allyloxy-1-(tert-butyldiphenylsilanyloxy)-8-ethyl-3-methoxymethoxy-4-(2-trityloxyethyl)-undeca-5,9-diene-4,7-diol

acryloyl chloride

2-(allyloxy)acetic acid

2-(allyloxy)-N-methoxy-N-methylacetamide

Downstream raw materials:

(5S,6S)-6-[(E)-(3R,4R)-6-(tert-butyldiphenylsilanyloxy)-3-hydroxy-4-methoxymethoxy-3-(2-trityloxyethyl)hex-1-en-1-yl]-5-ethyl-5,6-dihydropyran-2-one

C₅₄H₆₄O₇Si

(5S,6S)-6-[(E)-(3R,4R)-6-(tert-butyldiphenylsilanyloxy)-3-hydroxy-3-(2-hydroxyethyl)-4-methoxymethoxyhex-1-en-1-yl]-5-ethyl-5,6-dihydropyran-2-one

(5S,6S)-6-[(E)-(3R,4R)-3-(2-azidoethyl)-6-(tert-butyldiphenylsilanyloxy)-3-hydroxy-4-methoxymethoxyhex-1-en-1-yl]-5-ethyl-5,6-dihydro-pyran-2-one

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