N-((2aR,2a¹R,3R,3aS,6R,6aR)-3-methyl-4-((triisopropylsilyl)oxy)-2a,2a¹,3,3a,6,6a-hexahydro-2H-cyclobuta[cd]benzofuran-6-yl)-2-(phenylselenyl)acrylamide

Base Information

• Chemical Name: N-((2aR,2a¹R,3R,3aS,6R,6aR)-3-methyl-4-((triisopropylsilyl)oxy)-2a,2a¹,3,3a,6,6a-hexahydro-2H-cyclobuta[cd]benzofuran-6-yl)-2-(phenylselenyl)acrylamide
• CAS No.: 1421312-82-4
• Molecular Formula: C₂₈H₄₁NO₃SeSi
• Molecular Weight: 546.684
• Mol file: 1421312-82-4.mol

Synonyms:N-((2aR,2a¹R,3R,3aS,6R,6aR)-3-methyl-4-((triisopropylsilyl)oxy)-2a,2a¹,3,3a,6,6a-hexahydro-2H-cyclobuta[cd]benzofuran-6-yl)-2-(phenylselenyl)acrylamide

Chemical Property of N-((2aR,2a¹R,3R,3aS,6R,6aR)-3-methyl-4-((triisopropylsilyl)oxy)-2a,2a¹,3,3a,6,6a-hexahydro-2H-cyclobuta[cd]benzofuran-6-yl)-2-(phenylselenyl)acrylamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-((2aR,2a¹R,3R,3aS,6R,6aR)-3-methyl-4-((triisopropylsilyl)oxy)-2a,2a¹,3,3a,6,6a-hexahydro-2H-cyclobuta[cd]benzofuran-6-yl)-2-(phenylselenyl)acrylamide

There total 6 articles about N-((2aR,2a¹R,3R,3aS,6R,6aR)-3-methyl-4-((triisopropylsilyl)oxy)-2a,2a¹,3,3a,6,6a-hexahydro-2H-cyclobuta[cd]benzofuran-6-yl)-2-(phenylselenyl)acrylamide 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: 69.0%

C19H35NO2Si (1421312-76-6) + α-phenylselenoacrylic acid (77461-50-8) → N-((2aR,2a1R,3R,3aS,6R,6aR)-3-methyl-4-((triisopropylsilyl)oxy)-2a,2a1,3,3a,6,6a-hexahydro-2H-cyclobuta[cd]benzofuran-6-yl)-2-(phenylselenyl)acrylamide (1421312-82-4)

Guidance literature:

α-phenylselenoacrylic acid; With triethylamine; 3,5-dinitrobenoyl chloride; In dichloromethane; at 20 ℃; for 1h;

C₁₉H₃₅NO₂Si; With dmap; In dichloromethane; for 1h;

DOI:10.1021/ol400012s

Reference yield:

(S,E)-4-(but-2-en-1-yloxy)cyclohex-2-en-1-one (1421312-71-1) → N-((2aR,2a1R,3R,3aS,6R,6aR)-3-methyl-4-((triisopropylsilyl)oxy)-2a,2a1,3,3a,6,6a-hexahydro-2H-cyclobuta[cd]benzofuran-6-yl)-2-(phenylselenyl)acrylamide (1421312-82-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: dichloromethane / 2 h / 0 °C / Inert atmosphere; Irradiation; Photolysis

2.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.5 h / 0 - 20 °C

3.1: benzaldehyde; trimethylsilylazide / dichloromethane / 0.75 h / -19 °C

4.1: lithium aluminium tetrahydride / diethyl ether / 1 h / 0 °C

5.1: triethylamine; 3,5-dinitrobenoyl chloride / dichloromethane / 1 h / 20 °C

5.2: 1 h

With lithium aluminium tetrahydride; trimethylsilylazide; potassium hexamethylsilazane; benzaldehyde; triethylamine; 3,5-dinitrobenoyl chloride; In tetrahydrofuran; diethyl ether; dichloromethane; toluene;

DOI:10.1021/ol400012s

Reference yield:

(2aR,2a1R,3R,3aS,6aS)-3-methylhexahydro-2H-cyclobuta[cd]benzofuran-4(2aH)-one (1421312-72-2) → N-((2aR,2a1R,3R,3aS,6R,6aR)-3-methyl-4-((triisopropylsilyl)oxy)-2a,2a1,3,3a,6,6a-hexahydro-2H-cyclobuta[cd]benzofuran-6-yl)-2-(phenylselenyl)acrylamide (1421312-82-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.5 h / 0 - 20 °C

2.1: benzaldehyde; trimethylsilylazide / dichloromethane / 0.75 h / -19 °C

3.1: lithium aluminium tetrahydride / diethyl ether / 1 h / 0 °C

4.1: triethylamine; 3,5-dinitrobenoyl chloride / dichloromethane / 1 h / 20 °C

4.2: 1 h

With lithium aluminium tetrahydride; trimethylsilylazide; potassium hexamethylsilazane; benzaldehyde; triethylamine; 3,5-dinitrobenoyl chloride; In tetrahydrofuran; diethyl ether; dichloromethane; toluene;

DOI:10.1021/ol400012s

upstream raw materials:

(S)-(-)-4-hydroxy-2-cyclohexan-1-one

(S,E)-4-(but-2-en-1-yloxy)cyclohex-2-en-1-one

C₁₉H₃₅NO₂Si

α-phenylselenoacrylic acid

Downstream raw materials:

(2aR,2a¹R,3R,3aS,4aS,8aR,8bR)-3-methyl-6-(phenylselanyl)octahydro-2Hcyclobuta[3,4]benzofuro[7,6-b]pyridine-4,7(2aH,2a¹H)-dione

(2aR,2a¹R,3R,3aS,4aS,8aR,8bR)-3-methyl-6-(phenylselanyl)octahydro-2Hcyclobuta[3,4]benzofuro[7,6-b]pyridine-4,7(2aH,2a¹H)-dione