tert-butyl (1S,3aR,6aR)-octahydro-1-pentalenyl-[(4-methylphenyl)sulfonyl]carbamate

Base Information

• Chemical Name: tert-butyl (1S,3aR,6aR)-octahydro-1-pentalenyl-[(4-methylphenyl)sulfonyl]carbamate
• CAS No.: 612546-43-7
• Molecular Formula: C₂₀H₂₉NO₄S
• Molecular Weight: 379.521
• Mol file: 612546-43-7.mol

Synonyms:tert-butyl (1S,3aR,6aR)-octahydro-1-pentalenyl-[(4-methylphenyl)sulfonyl]carbamate

Chemical Property of tert-butyl (1S,3aR,6aR)-octahydro-1-pentalenyl-[(4-methylphenyl)sulfonyl]carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (1S,3aR,6aR)-octahydro-1-pentalenyl-[(4-methylphenyl)sulfonyl]carbamate

There total 4 articles about tert-butyl (1S,3aR,6aR)-octahydro-1-pentalenyl-[(4-methylphenyl)sulfonyl]carbamate 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:

(1R,3aR,6aR)-octahydro-1-pentalenol (612546-41-5) + N-[(tert-butoxy)carbonyl]-4-methylbenzenesulfonamide (18303-04-3) → tert-butyl (1S,3aR,6aR)-octahydro-1-pentalenyl-[(4-methylphenyl)sulfonyl]carbamate (612546-43-7)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; at 20 ℃; for 65h;

DOI:10.1016/S0040-4039(03)01677-0

Reference yield:

Cyclooctene oxide (286-62-4) → tert-butyl (1S,3aR,6aR)-octahydro-1-pentalenyl-[(4-methylphenyl)sulfonyl]carbamate (612546-43-7)

Guidance literature:

Multi-step reaction with 4 steps

1: sec-BuLi; (-)-sparteine / diethyl ether / -78 - 20 °C

2: PPh₃; DEAD / 65 h / 20 °C

3: KOH / tetrahydrofuran; methanol / 0.67 h / 0 °C

4: PPh₃; DEAD / 65 h / 20 °C

With potassium hydroxide; sec.-butyllithium; triphenylphosphine; (-)-sparteine; diethylazodicarboxylate; In tetrahydrofuran; methanol; diethyl ether; 2: Mitsunobu reaction / 4: Mitsunobu reaction;

DOI:10.1016/S0040-4039(03)01677-0

Reference yield:

(-)-cis-bicyclo<3.3.0>octan-endo-2-ol (85717-58-4) → tert-butyl (1S,3aR,6aR)-octahydro-1-pentalenyl-[(4-methylphenyl)sulfonyl]carbamate (612546-43-7)

Guidance literature:

Multi-step reaction with 3 steps

1: PPh₃; DEAD / 65 h / 20 °C

2: KOH / tetrahydrofuran; methanol / 0.67 h / 0 °C

3: PPh₃; DEAD / 65 h / 20 °C

With potassium hydroxide; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; 1: Mitsunobu reaction / 3: Mitsunobu reaction;

DOI:10.1016/S0040-4039(03)01677-0

upstream raw materials:

(1R,3aR,6aR)-octahydro-1-pentalenol

N-[(tert-butoxy)carbonyl]-4-methylbenzenesulfonamide

Cyclooctene oxide

(-)-cis-bicyclo<3.3.0>octan-endo-2-ol