(2S,4aS,5R,8aR)-5-Methyl-2-propyl-4-trifluoromethanesulfonyloxy-4a,5,6,7,8,8a-hexahydro-2H-quinoline-1-carboxylic acid phenyl ester

Base Information

• Chemical Name: (2S,4aS,5R,8aR)-5-Methyl-2-propyl-4-trifluoromethanesulfonyloxy-4a,5,6,7,8,8a-hexahydro-2H-quinoline-1-carboxylic acid phenyl ester
• CAS No.: 154569-08-1
• Molecular Formula: C₂₁H₂₆F₃NO₅S
• Molecular Weight: 461.502
• Mol file: 154569-08-1.mol

Synonyms:

Chemical Property of (2S,4aS,5R,8aR)-5-Methyl-2-propyl-4-trifluoromethanesulfonyloxy-4a,5,6,7,8,8a-hexahydro-2H-quinoline-1-carboxylic acid phenyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4aS,5R,8aR)-5-Methyl-2-propyl-4-trifluoromethanesulfonyloxy-4a,5,6,7,8,8a-hexahydro-2H-quinoline-1-carboxylic acid phenyl ester

There total 8 articles about (2S,4aS,5R,8aR)-5-Methyl-2-propyl-4-trifluoromethanesulfonyloxy-4a,5,6,7,8,8a-hexahydro-2H-quinoline-1-carboxylic acid phenyl 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: 78.0%

N,N-phenylbistrifluoromethane-sulfonimide (37595-74-7) + (2S,4aS,5R,8aR)-N-phenoxycarbonyl-2-propyl-5-methyl-decahydroquinolin-4-one (154569-07-0) → (2S,4aS,5R,8aR)-5-Methyl-2-propyl-4-trifluoromethanesulfonyloxy-4a,5,6,7,8,8a-hexahydro-2H-quinoline-1-carboxylic acid phenyl ester (154569-08-1)

Guidance literature:

With lithium diisopropyl amide;

DOI:10.1039/c39930001838

Reference yield:

(R)-2-Pent-4-enyl-2,3-dihydro-1H-pyridin-4-one (154467-63-7) → (2S,4aS,5R,8aR)-5-Methyl-2-propyl-4-trifluoromethanesulfonyloxy-4a,5,6,7,8,8a-hexahydro-2H-quinoline-1-carboxylic acid phenyl ester (154569-08-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 99 percent / n-BuLi

2: 88 percent / BF₃*OEt₂, CuBr / -78 °C

3: 83 percent / NaIO₄, OsO₄

4: 81 percent / p-toluenesulfonic acid / benzene / 2.5 h / 47 °C

5: 87 percent / 1.) BF₃*OEt₂, 2.) MeOH

6: 78 percent / LDA

With methanol; sodium periodate; osmium(VIII) oxide; n-butyllithium; boron trifluoride diethyl etherate; toluene-4-sulfonic acid; copper(I) bromide; lithium diisopropyl amide; In benzene;

DOI:10.1039/c39930001838

Reference yield:

(R)-4-Oxo-2-pent-4-enyl-5-triisopropylsilanyl-3,4-dihydro-2H-pyridine-1-carboxylic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester (154467-62-6) → (2S,4aS,5R,8aR)-5-Methyl-2-propyl-4-trifluoromethanesulfonyloxy-4a,5,6,7,8,8a-hexahydro-2H-quinoline-1-carboxylic acid phenyl ester (154569-08-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) NaOMe, 2.) oxalic acid / 1.) MeOH

2: 99 percent / n-BuLi

3: 88 percent / BF₃*OEt₂, CuBr / -78 °C

4: 83 percent / NaIO₄, OsO₄

5: 81 percent / p-toluenesulfonic acid / benzene / 2.5 h / 47 °C

6: 87 percent / 1.) BF₃*OEt₂, 2.) MeOH

7: 78 percent / LDA

With methanol; sodium periodate; osmium(VIII) oxide; n-butyllithium; boron trifluoride diethyl etherate; sodium methylate; oxalic acid; toluene-4-sulfonic acid; copper(I) bromide; lithium diisopropyl amide; In benzene;

DOI:10.1039/c39930001838

upstream raw materials:

N,N-phenylbistrifluoromethane-sulfonimide

(2S,4aS,5R,8aR)-N-phenoxycarbonyl-2-propyl-5-methyl-decahydroquinolin-4-one

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

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

Downstream raw materials:

(-)-pumiliotoxin C