Phosphoric acid diethyl ester (3S,5S)-5-isopropenyl-2,3-dimethyl-cyclohex-1-enyl ester

Base Information

• Chemical Name: Phosphoric acid diethyl ester (3S,5S)-5-isopropenyl-2,3-dimethyl-cyclohex-1-enyl ester
• CAS No.: 151324-22-0
• Molecular Formula: C₁₅H₂₇O₄P
• Molecular Weight: 302.351
• Mol file: 151324-22-0.mol

Synonyms:Phosphoric acid diethyl ester (3S,5S)-5-isopropenyl-2,3-dimethyl-cyclohex-1-enyl ester

Chemical Property of Phosphoric acid diethyl ester (3S,5S)-5-isopropenyl-2,3-dimethyl-cyclohex-1-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Phosphoric acid diethyl ester (3S,5S)-5-isopropenyl-2,3-dimethyl-cyclohex-1-enyl ester

There total 1 articles about Phosphoric acid diethyl ester (3S,5S)-5-isopropenyl-2,3-dimethyl-cyclohex-1-enyl 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: 86.0%

(S)-p-mentha-6,8-dien-2-one (2244-16-8,6485-40-1) + diethyl chlorophosphate (814-49-3) → Phosphoric acid diethyl ester (3S,5S)-5-isopropenyl-2,3-dimethyl-cyclohex-1-enyl ester (151324-22-0)

Guidance literature:

(S)-p-mentha-6,8-dien-2-one; Li(CH₃)2Cu; In diethyl ether; at 0 - 20 ℃;

diethyl chlorophosphate; In N,N,N,N,N,N-hexamethylphosphoric triamide; at 50 ℃; for 12h; Further stages.;

DOI:10.1021/ja0208456

Reference yield: 62.0%

methanol (67-56-1) + Phosphoric acid diethyl ester (3S,5S)-5-isopropenyl-2,3-dimethyl-cyclohex-1-enyl ester (151324-22-0) → (1S,5R)-3-(Diethoxy-phosphoryloxy)-4,5-dimethyl-cyclohex-3-enecarboxylic acid methyl ester + (1S,5S)-3-(Diethoxy-phosphoryloxy)-4,5-dimethyl-cyclohex-3-enecarboxylic acid methyl ester

Guidance literature:

methanol; Phosphoric acid diethyl ester (3S,5S)-5-isopropenyl-2,3-dimethyl-cyclohex-1-enyl ester; With pyridine; ozone; In dichloromethane; at 20 ℃;

With pyridine; 4-nitro-benzoyl chloride; In dichloromethane; for 24h; Further stages.; Heating;

DOI:10.1021/ja0208456

Reference yield:

Phosphoric acid diethyl ester (3S,5S)-5-isopropenyl-2,3-dimethyl-cyclohex-1-enyl ester (151324-22-0) → (1S,5S)-4,5-Dimethyl-cyclohex-3-enol (151433-56-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: O₃; pyridine / CH₂Cl₂ / 20 °C

1.2: 62 percent / p-NO₂-C₆H₄COCl; pyridine / CH₂Cl₂ / 24 h / Heating

2.1: Li; MeNH₂ / tetrahydrofuran; 2-methyl-propan-2-ol / -78 - -15 °C

3.1: H₂CrO₄ / diethyl ether / 2 h / 0 °C

4.1: LiAlH₄ / diethyl ether / -78 °C

With pyridine; lithium aluminium tetrahydride; chromic acid; lithium; ozone; methylamine; In tetrahydrofuran; diethyl ether; dichloromethane; tert-butyl alcohol;

DOI:10.1021/ja0208456

upstream raw materials:

(S)-p-mentha-6,8-dien-2-one

diethyl chlorophosphate

Downstream raw materials:

Acetic acid (1S,5S)-3-(diethoxy-phosphoryloxy)-4,5-dimethyl-cyclohex-3-enyl ester

(1S,5S)-4,5-Dimethyl-cyclohex-3-enol

(1R,3S,4R,5S)-3,4-diiodomethyl-4,5-dimethylcyclohexan-1-ol

(1R,3S,4R,5S)-3,4-diiodomethyl-4,5-dimethylcyclohexan-1-one