(5E,7E)-(3S)-3β-t-butyldimethylsilyloxy-9,10-secocholesta-5,7,10(19)-trien-1α-yl 2-propenoate

Base Information

• Chemical Name: (5E,7E)-(3S)-3β-t-butyldimethylsilyloxy-9,10-secocholesta-5,7,10(19)-trien-1α-yl 2-propenoate
• CAS No.: 1021498-34-9
• Molecular Formula: C₃₆H₆₀O₃Si
• Molecular Weight: 568.956
• Mol file: 1021498-34-9.mol

Synonyms:(5E,7E)-(3S)-3β-t-butyldimethylsilyloxy-9,10-secocholesta-5,7,10(19)-trien-1α-yl 2-propenoate

Chemical Property of (5E,7E)-(3S)-3β-t-butyldimethylsilyloxy-9,10-secocholesta-5,7,10(19)-trien-1α-yl 2-propenoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5E,7E)-(3S)-3β-t-butyldimethylsilyloxy-9,10-secocholesta-5,7,10(19)-trien-1α-yl 2-propenoate

There total 1 articles about (5E,7E)-(3S)-3β-t-butyldimethylsilyloxy-9,10-secocholesta-5,7,10(19)-trien-1α-yl 2-propenoate 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: 46.0%

acryloyl chloride (814-68-6,25189-84-8) + (1S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-3-[2-[(1R,3aS,7aR)-1-((R)-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(E)-ylidene]-2-methylene-cyclohexanol → (5E,7E)-(3S)-3β-t-butyldimethylsilyloxy-9,10-secocholesta-5,7,10(19)-trien-1α-yl 2-propenoate (1021498-34-9)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1016/j.steroids.2007.03.005

Reference yield:

(5E,7E)-(3S)-3β-t-butyldimethylsilyloxy-9,10-secocholesta-5,7,10(19)-trien-1α-yl 2-propenoate (1021498-34-9) → (5E,7E)-(3S)-3β-t-butyldimethylsilyloxy-19-hydroxymethyl-9,10-secocholesta-5,7-dien-1-α-ol (1021498-45-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 40 percent / Hoveyda second generation catalyst / toluene / 4 h / 80 °C

2: 88 percent / LiAlH₄ / tetrahydrofuran / 0.5 h / 0 °C

With lithium aluminium tetrahydride; Hoveyda-Grubbs catalyst second generation; In tetrahydrofuran; toluene;

DOI:10.1016/j.steroids.2007.03.005

Reference yield:

(5E,7E)-(3S)-3β-t-butyldimethylsilyloxy-9,10-secocholesta-5,7,10(19)-trien-1α-yl 2-propenoate (1021498-34-9) → (5E,7E)-(3S)-19-hydroxymethyl-9,10-secocholesta-5,7-diene-1α,3β-diol

Guidance literature:

Multi-step reaction with 3 steps

1: 40 percent / Hoveyda second generation catalyst / toluene / 4 h / 80 °C

2: 88 percent / LiAlH₄ / tetrahydrofuran / 0.5 h / 0 °C

3: 89 percent / TBAF / tetrahydrofuran / 0.5 h / 20 °C

With lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; Hoveyda-Grubbs catalyst second generation; In tetrahydrofuran; toluene;

DOI:10.1016/j.steroids.2007.03.005

upstream raw materials:

acryloyl chloride

Downstream raw materials:

(5E,7E)-(3S)-3β-t-butyldimethylsilyloxy-19-hydroxymethyl-9,10-secocholesta-5,7-dien-1-α-ol