(3R,4R)-4-acetyl-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-methylcyclohexan-1-one

Base Information

• Chemical Name: (3R,4R)-4-acetyl-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-methylcyclohexan-1-one
• CAS No.: 862973-14-6
• Molecular Formula: C₁₄H₂₂O₄
• Molecular Weight: 254.326
• Mol file: 862973-14-6.mol

Synonyms:(3R,4R)-4-acetyl-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-methylcyclohexan-1-one

Chemical Property of (3R,4R)-4-acetyl-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-methylcyclohexan-1-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4R)-4-acetyl-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-methylcyclohexan-1-one

There total 2 articles about (3R,4R)-4-acetyl-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-methylcyclohexan-1-one 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: 89.0%

(4R,5R)-4-acetyl-5-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-methyl-2-cyclohexen-1-one (862973-12-4) → (3R,4R)-4-acetyl-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-methylcyclohexan-1-one (862973-14-6)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; at 20 ℃; for 12h;

DOI:10.1055/s-2005-869843

Reference yield:

(E)-1,3,4-trideoxy-5,6-O-isopropylidene-3-C-methyl-D-glycero-hex-3-eno-2-ulose (82042-36-2) → (3R,4R)-4-acetyl-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-methylcyclohexan-1-one (862973-14-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: toluene / 72 h / 150 °C

1.2: 66 percent / aq. HCl / tetrahydrofuran / 0.5 h / 20 °C

2.1: 89 percent / H₂ / Pd/C / ethyl acetate / 10 h / 20 °C / 760 Torr

With hydrogen; palladium on activated charcoal; In ethyl acetate; toluene; 1.1: intermolecular Diels-Alder reaction;

DOI:10.1021/jo0610208

Reference yield: 75.0%

(3R,4R)-4-acetyl-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-methylcyclohexan-1-one (862973-14-6) + methanol (67-56-1) → 1-[(1R,2R)-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-4,4-dimethoxy-1-methylcyclohexyl]ethan-1-one (862973-15-7)

Guidance literature:

With pyridinium p-toluenesulfonate; at 0 ℃; for 2.5h;

DOI:10.1055/s-2005-869843 DOI:10.1021/jo0610208

upstream raw materials:

(4R,5R)-4-acetyl-5-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-methyl-2-cyclohexen-1-one

(E)-1,3,4-trideoxy-5,6-O-isopropylidene-3-C-methyl-D-glycero-hex-3-eno-2-ulose

Downstream raw materials:

1-[(1R,2R)-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-4,4-dimethoxy-1-methylcyclohexyl]ethan-1-one

(4S)-4-[(1R,2R)-5,5-dimethoxy-2-methyl-2-(1-propynyl)cyclohexyl]-2,2-dimethyl-1,3-dioxolane

(4S)-4-[(1R,2R)-2-[(1E)-2-iodo-1-propenyl]-5,5-dimethoxy-2-methylcyclohexyl]-2,2-dimethyl-1,3-dioxolane

Trifluoro-methanesulfonic acid 1-[(1R,2R)-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4,4-dimethoxy-1-methyl-cyclohexyl]-vinyl ester