<3S-(E)>-4-(4-hydroxy-3-methyl-1-butenyl)-1-<(4-methylphenyl)sulfonyl>-1H-indole

Base Information

• Chemical Name: <3S-(E)>-4-(4-hydroxy-3-methyl-1-butenyl)-1-<(4-methylphenyl)sulfonyl>-1H-indole
• CAS No.: 79681-06-4
• Molecular Formula: C₂₀H₂₁NO₃S
• Molecular Weight: 355.458
• Mol file: 79681-06-4.mol

Synonyms:<3S-(E)>-4-(4-hydroxy-3-methyl-1-butenyl)-1-<(4-methylphenyl)sulfonyl>-1H-indole

Chemical Property of <3S-(E)>-4-(4-hydroxy-3-methyl-1-butenyl)-1-<(4-methylphenyl)sulfonyl>-1H-indole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of <3S-(E)>-4-(4-hydroxy-3-methyl-1-butenyl)-1-<(4-methylphenyl)sulfonyl>-1H-indole

There total 11 articles about <3S-(E)>-4-(4-hydroxy-3-methyl-1-butenyl)-1-<(4-methylphenyl)sulfonyl>-1H-indole 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: 6.2%

(R)-(+)-(3-hydroxy-2-methyl-1-propyl)triphenylphosphonium bromide (81658-47-1) + 1-[(4-methyl-phenyl)-sulfonyl]-1H-indol-4-carboxaldehyde (79681-04-2) → <3S-(E)>-4-(4-hydroxy-3-methyl-1-butenyl)-1-<(4-methylphenyl)sulfonyl>-1H-indole (79681-06-4,93290-78-9) + <3S-(E)>-4-(4-hydroxy-3-methyl-1-butenyl)-1-<(4-methylphenyl)sulfonyl>-1H-indole (79681-06-4)

Guidance literature:

With n-butyllithium; Yield given. Multistep reaction; 1.) THF, hexane, -78 deg C - RT, 3 h; 2.) -78 deg C - RT, 2h;

DOI:10.1016/0040-4020(84)80018-6

Reference yield: 6.2%

(R)-(+)-(3-hydroxy-2-methyl-1-propyl)triphenylphosphonium bromide (81658-47-1) + 1-[(4-methyl-phenyl)-sulfonyl]-1H-indol-4-carboxaldehyde (79681-04-2) → <3S-(E)>-4-(4-hydroxy-3-methyl-1-butenyl)-1-<(4-methylphenyl)sulfonyl>-1H-indole (79681-06-4,93290-78-9) + <3S-(E)>-4-(4-hydroxy-3-methyl-1-butenyl)-1-<(4-methylphenyl)sulfonyl>-1H-indole (79681-06-4)

Guidance literature:

With n-butyllithium; Yield given. Multistep reaction; 1.) THF, hexane, -78 deg C - RT, 3 h; 2.) -78 deg C - RT, 2h;

DOI:10.1016/0040-4020(84)80018-6

Reference yield:

methyl 1H-indole-4-carboxylate (39830-66-5) → <3S-(E)>-4-(4-hydroxy-3-methyl-1-butenyl)-1-<(4-methylphenyl)sulfonyl>-1H-indole (79681-06-4,93290-78-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 92.4 percent / K₂CO₃ / butan-2-one / 24 h / Heating

2: 85.3 percent / lithium aluminium hydride / tetrahydrofuran / 0.75 h / 0 - 5 °C

3: 96.6 percent / pyridinium chlorochromate, sodium acetate / CH₂Cl₂ / 2.5 h / Ambient temperature

4: 6.2 percent / 1.) n-butyllithium / 1.) THF, hexane, -78 deg C - RT, 3 h; 2.) -78 deg C - RT, 2h

With lithium aluminium tetrahydride; n-butyllithium; sodium acetate; potassium carbonate; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; butanone;

DOI:10.1016/0040-4020(84)80018-6

upstream raw materials:

(R)-(+)-(3-hydroxy-2-methyl-1-propyl)triphenylphosphonium bromide

1-[(4-methyl-phenyl)-sulfonyl]-1H-indol-4-carboxaldehyde

methyl 1H-indole-4-carboxylate

4-(hydroxymethyl)-1-<(4-methylphenyl)sulfonyl>-1H-indole

Downstream raw materials:

<9S-<9β(S*),9aβ>>-4-acetyl-4,6,9,9a-tetrahydro-9-<1-methyl-2-(phenylseleno)ethyl>indolo<4,3-ef><2,1>-benzisoxazole

<9R-<9α(S*),9aα>>-4-acetyl-4,6,9,9a-tetrahydro-9-<1-methyl-2-(phenylseleno)ethyl>indolo<4,3-ef><2,1>-benzisoxazole

(+)-paliclavine

<3-S-(E)>-4-<3-methyl-4-<(tetrahydro-2H-pyran-2yl)oxy>-1-butenyl>-1-<(4-methylphenyl)sulfonyl>-1H-indole