(2S,4aS,5R,8aS)-2,5-Bis-[3-(2-nitro-phenylselanyl)-propyl]-octahydro-quinoline-1-carboxylic acid benzyl ester

Base Information

• Chemical Name: (2S,4aS,5R,8aS)-2,5-Bis-[3-(2-nitro-phenylselanyl)-propyl]-octahydro-quinoline-1-carboxylic acid benzyl ester
• CAS No.: 161693-59-0
• Molecular Formula: C₃₅H₄₁N₃O₆Se₂
• Molecular Weight: 757.647

Synonyms:(2S,4aS,5R,8aS)-2,5-Bis-[3-(2-nitro-phenylselanyl)-propyl]-octahydro-quinoline-1-carboxylic acid benzyl ester

Chemical Property of (2S,4aS,5R,8aS)-2,5-Bis-[3-(2-nitro-phenylselanyl)-propyl]-octahydro-quinoline-1-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of (2S,4aS,5R,8aS)-2,5-Bis-[3-(2-nitro-phenylselanyl)-propyl]-octahydro-quinoline-1-carboxylic acid benzyl ester

There total 14 articles about (2S,4aS,5R,8aS)-2,5-Bis-[3-(2-nitro-phenylselanyl)-propyl]-octahydro-quinoline-1-carboxylic acid benzyl 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: 79.0%

p-nitrophenyl selenocyanate (19188-18-2) + (2S,5R,8aS)-2,5-Bis-(3-hydroxy-propyl)-octahydro-quinoline-1-carboxylic acid benzyl ester → (2S,4aR,5R,8aS)-2,5-Bis-[3-(2-nitro-phenylselanyl)-propyl]-octahydro-quinoline-1-carboxylic acid benzyl ester + (2S,4aS,5R,8aS)-2,5-Bis-[3-(2-nitro-phenylselanyl)-propyl]-octahydro-quinoline-1-carboxylic acid benzyl ester (161693-59-0)

Guidance literature:

With tributylphosphine; In dichloromethane; Yield given. Title compound not separated from byproducts;

DOI:10.1021/jo00109a006

Reference yield:

(S)-2-Pent-4-enyl-2,3-dihydro-1H-pyridin-4-one (161693-50-1) → (2S,4aS,5R,8aS)-2,5-Bis-[3-(2-nitro-phenylselanyl)-propyl]-octahydro-quinoline-1-carboxylic acid benzyl ester (161693-59-0)

Guidance literature:

Multi-step reaction with 12 steps

1: 93 percent / n-BuLi

2: 79 percent / CuBr, BF₃*OEt₂ / -78 °C

3: 88 percent / NaIO₄ / OsO₄

4: 92 percent / TsOH / benzene / 52 °C

6: 86 percent / Bu₃N, HCO₂H / (Ph₃P)Pd(OAc)2

7: 87 percent / aq. KOH / propan-2-ol / 144 h / Heating

8: H₂ / 5percent Pt/C / ethanol

9: H₂ / Pd(OH)2 / ethanol

10: NaOH

11: K₂CO₃ / methanol

12: 79 percent / Bu₃P / CH₂Cl₂

With potassium hydroxide; sodium hydroxide; sodium periodate; n-butyllithium; formic acid; tributyl-amine; tributylphosphine; boron trifluoride diethyl etherate; hydrogen; potassium carbonate; toluene-4-sulfonic acid; copper(I) bromide; palladium dihydroxide; osmium(VIII) oxide; platinum on activated charcoal; Pd(PPh₃)(OAc)2; In methanol; ethanol; dichloromethane; isopropyl alcohol; benzene;

DOI:10.1021/jo00109a006

Reference yield:

(S)-4-Oxo-2-pent-4-enyl-3,4-dihydro-2H-pyridine-1-carboxylic acid phenyl ester (161755-27-7) → (2S,4aS,5R,8aS)-2,5-Bis-[3-(2-nitro-phenylselanyl)-propyl]-octahydro-quinoline-1-carboxylic acid benzyl ester (161693-59-0)

Guidance literature:

Multi-step reaction with 11 steps

1: 79 percent / CuBr, BF₃*OEt₂ / -78 °C

2: 88 percent / NaIO₄ / OsO₄

3: 92 percent / TsOH / benzene / 52 °C

5: 86 percent / Bu₃N, HCO₂H / (Ph₃P)Pd(OAc)2

6: 87 percent / aq. KOH / propan-2-ol / 144 h / Heating

7: H₂ / 5percent Pt/C / ethanol

8: H₂ / Pd(OH)2 / ethanol

9: NaOH

10: K₂CO₃ / methanol

11: 79 percent / Bu₃P / CH₂Cl₂

With potassium hydroxide; sodium hydroxide; sodium periodate; formic acid; tributyl-amine; tributylphosphine; boron trifluoride diethyl etherate; hydrogen; potassium carbonate; toluene-4-sulfonic acid; copper(I) bromide; palladium dihydroxide; osmium(VIII) oxide; platinum on activated charcoal; Pd(PPh₃)(OAc)2; In methanol; ethanol; dichloromethane; isopropyl alcohol; benzene;

DOI:10.1021/jo00109a006

upstream raw materials:

p-nitrophenyl selenocyanate

(S)-2-Pent-4-enyl-2,3-dihydro-1H-pyridin-4-one

(S)-4-Oxo-2-pent-4-enyl-3,4-dihydro-2H-pyridine-1-carboxylic acid phenyl ester

(2R,5R,8aS)-2,5-Bis-(3-benzyloxy-propyl)-1,2,3,5,6,7,8,8a-octahydro-quinoline

Downstream raw materials:

(2S,4aS,5R,8aS)-2,5-Diallyl-octahydro-quinoline-1-carboxylic acid benzyl ester

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