tert-butyl (1S,4R,5S)-4-hydroxy-5-methylcyclohex-2-enyl carbonate

Base Information

• Chemical Name: tert-butyl (1S,4R,5S)-4-hydroxy-5-methylcyclohex-2-enyl carbonate
• CAS No.: 1092513-27-3
• Molecular Formula: C₁₂H₂₀O₄
• Molecular Weight: 228.288
• Mol file: 1092513-27-3.mol

Synonyms:tert-butyl (1S,4R,5S)-4-hydroxy-5-methylcyclohex-2-enyl carbonate

Chemical Property of tert-butyl (1S,4R,5S)-4-hydroxy-5-methylcyclohex-2-enyl carbonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (1S,4R,5S)-4-hydroxy-5-methylcyclohex-2-enyl carbonate

There total 4 articles about tert-butyl (1S,4R,5S)-4-hydroxy-5-methylcyclohex-2-enyl carbonate 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: 90.0%

tert-butyl (1S,5S)-5-methyl-4-oxocyclohex-2-enyl carbonate (954390-26-2) → tert-butyl (1S,4S,5S)-4-hydroxy-5-methylcyclohex-2-enyl carbonate + tert-butyl (1S,4R,5S)-4-hydroxy-5-methylcyclohex-2-enyl carbonate (1092513-27-3)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at -78 ℃; for 0.5h; optical yield given as %de; diastereoselective reaction;

DOI:10.1055/s-2008-1067262

Reference yield: 90.0%

tert-butyl (1S,5S)-5-methyl-4-oxocyclohex-2-enyl carbonate (954390-26-2) → tert-butyl (1S,4R,5S)-4-hydroxy-5-methylcyclohex-2-enyl carbonate (1092513-27-3)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at -78 ℃;

DOI:10.1002/ijch.202100015

Reference yield:

(2S,4S,5R)-4,5-dihydroxy-2-methyl cyclohexanone (1043454-50-7) → tert-butyl (1S,4R,5S)-4-hydroxy-5-methylcyclohex-2-enyl carbonate (1092513-27-3)

Guidance literature:

Multi-step reaction with 2 steps

1: dmap / dichloromethane

2: lithium aluminium tetrahydride / tetrahydrofuran / -78 °C

With dmap; lithium aluminium tetrahydride; In tetrahydrofuran; dichloromethane;

DOI:10.1002/ijch.202100015

upstream raw materials:

tert-butyl (1S,5S)-5-methyl-4-oxocyclohex-2-enyl carbonate

(2S,4S,5R)-4,5-dihydroxy-2-methyl cyclohexanone

di-tert-butyl dicarbonate

Downstream raw materials:

tert-butyl (1S,2S,3S,4R,5S)-2,3,4-trihydroxy-5-methylcyclohexyl carbonate