diethyl 2α,4α-dimethyl-5β-hydroxy-6-cyclohexenyl phosphate

Base Information

• Chemical Name: diethyl 2α,4α-dimethyl-5β-hydroxy-6-cyclohexenyl phosphate
• CAS No.: 79722-63-7
• Molecular Formula: C₁₂H₂₃O₅P
• Molecular Weight: 278.285
• Mol file: 79722-63-7.mol

Synonyms:

Chemical Property of diethyl 2α,4α-dimethyl-5β-hydroxy-6-cyclohexenyl phosphate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of diethyl 2α,4α-dimethyl-5β-hydroxy-6-cyclohexenyl phosphate

There total 1 articles about diethyl 2α,4α-dimethyl-5β-hydroxy-6-cyclohexenyl phosphate 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:

(2R,3R,4S)-4-methyl-2,3-epoxy-cyclohexanone (79767-70-7) → diethyl 2α,4α-dimethyl-5β-hydroxy-6-cyclohexenyl phosphate (79722-63-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) n-BuLi, diisopropylamine / 1.) THF, -78 deg C, 30 min, 2.) a) -78 deg C, b) room temperature, 30 min

2: 1.) cuprous cyanide / 1.) ether, -78 deg C, 1 h, 2.) a) -78 deg C, 1 h, b) -78 deg C -> room temperature

With n-butyllithium; copper(l) cyanide; diisopropylamine;

DOI:10.1021/jo00339a026

Reference yield: 76.0%

diethyl 2α,4α-dimethyl-5β-hydroxy-6-cyclohexenyl phosphate (79722-63-7) → 2α,4α-dimethyl-5-cyclohexen-1β-ol (79722-64-8)

Guidance literature:

With ammonia; lithium; for 0.5h;

DOI:10.1021/jo00339a026

Reference yield:

diethyl 2α,4α-dimethyl-5β-hydroxy-6-cyclohexenyl phosphate (79722-63-7) → α-multistriatin (54815-06-4)

Guidance literature:

Multi-step reaction with 9 steps

1: 76 percent / Li, liq. NH₃ / 0.5 h

2: 75 percent / MCPBA / CH₂Cl₂ / 20 h / Ambient temperature

3: 73 percent / CrO₃, pyridine / CH₂Cl₂ / 1.5 h / Ambient temperature

4: 1.) n-BuLi, diisopropylamine / 1.) THF, hexane, 0 deg C, 15 min, 2.) room temperature, 2 h

5: 1.) cuprous cyanide / 1.) ether, -78 deg C, 30 min, 2.) -78 deg C, 1 h

6: 98 percent / pyridine / CH₂Cl₂ / 2 h / 0 °C

7: 1.) O₃, 2.) LiAlH₄ / 1.) ether, -78 deg C, 2.) ether, room temperature, 2 h

8: p-toluenesulfonic acid / 15 h / Ambient temperature

9: Jones reagent / acetone / 1 h / 0 °C

With pyridine; chromium(VI) oxide; lithium aluminium tetrahydride; n-butyllithium; jones reagent; ammonia; copper(l) cyanide; lithium; toluene-4-sulfonic acid; ozone; diisopropylamine; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; acetone;

DOI:10.1021/jo00339a026

upstream raw materials:

(2R,3R,4S)-4-methyl-2,3-epoxy-cyclohexanone

Downstream raw materials:

2α,4α-dimethyl-5-cyclohexen-1β-ol

α-multistriatin