(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

Base Information

• Chemical Name: (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
• CAS No.: 1421312-94-8
• Molecular Formula: C₁₉H₂₁NO₃Se
• Molecular Weight: 390.341
• Mol file: 1421312-94-8.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 8 articles about (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 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: 40.0%

(1R,1aR,1a1R,3aR,4R,4aR,6R,6aR,6bS)-1-methyl-6-(phenylselenyl)-6a-((triisopropylsilyl)oxy)decahydro-1H-4,6-(epiminomethano)dicyclobuta[cd,f ]benzofuran-7-one → (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 (1421312-94-8) + (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 (1421312-84-6)

Guidance literature:

With nitromethane; hydrogen fluoride; In water; at 20 ℃; for 2h;

DOI:10.1021/acs.joc.5b01619

Reference yield:

(1R,1aR,1a1R,3aR,4aR,6R,6bS)-1-methyl-6-(phenylselanyl)-6a-((triisopropylsilyl)oxy)decahydro-1H-4,6-(epiminomethano)dicyclobuta[cd,f]benzofuran-7-one → (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 (1421312-94-8) + (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 (1421312-84-6)

Guidance literature:

With hydrogen fluoride; In nitromethane; water; at 20 ℃; for 2h;

DOI:10.1021/ol400012s

Reference yield:

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) → (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 (1421312-94-8) + (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 (1421312-84-6)

Guidance literature:

Multi-step reaction with 2 steps

1: trimethylaluminum / dichloromethane; hexane / 38 h / 80 °C

2: hydrogen fluoride / water; nitromethane / 2 h / 20 °C

With hydrogen fluoride; trimethylaluminum; In nitromethane; hexane; dichloromethane; water;

DOI:10.1021/ol400012s

upstream raw materials:

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

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

(2aR,2a¹R,3R,3aS,6aS)-3-methylhexahydro-2H-cyclobuta[cd]benzofuran-4(2aH)-one

C₁₉H₃₄O₂Si