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

Base Information

• Chemical Name: (4S)-4-[(1R,2R)-5,5-dimethoxy-2-methyl-2-(1-propynyl)cyclohexyl]-2,2-dimethyl-1,3-dioxolane
• CAS No.: 862973-11-3
• Molecular Formula: C₁₇H₂₈O₄
• Molecular Weight: 296.407
• Mol file: 862973-11-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 4 articles about (4S)-4-[(1R,2R)-5,5-dimethoxy-2-methyl-2-(1-propynyl)cyclohexyl]-2,2-dimethyl-1,3-dioxolane 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:

(4R,5R)-4-acetyl-5-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-methyl-2-cyclohexen-1-one (862973-12-4) → (4S)-4-[(1R,2R)-5,5-dimethoxy-2-methyl-2-(1-propynyl)cyclohexyl]-2,2-dimethyl-1,3-dioxolane (862973-11-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 89 percent / H₂ / Pd/C / ethyl acetate / 10 h / 20 °C / 760 Torr

2.1: 75 percent / PPTS / 2.5 h / 0 °C

3.1: KN(SiMe₃)2 / toluene; tetrahydrofuran / 1 h / -78 °C

4.1: LDA / tetrahydrofuran; hexane / 0.25 h / -78 °C

4.2: 435 mg / tetrahydrofuran; hexane / 1 h / 0 °C

With hydrogen; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; hexane; ethyl acetate; toluene;

DOI:10.1021/jo0610208

Reference yield:

(E)-1,3,4-trideoxy-5,6-O-isopropylidene-3-C-methyl-D-glycero-hex-3-eno-2-ulose (82042-36-2) → (4S)-4-[(1R,2R)-5,5-dimethoxy-2-methyl-2-(1-propynyl)cyclohexyl]-2,2-dimethyl-1,3-dioxolane (862973-11-3)

Guidance literature:

Multi-step reaction with 5 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

3.1: 75 percent / PPTS / 2.5 h / 0 °C

4.1: KN(SiMe₃)2 / toluene; tetrahydrofuran / 1 h / -78 °C

5.1: LDA / tetrahydrofuran; hexane / 0.25 h / -78 °C

5.2: 435 mg / tetrahydrofuran; hexane / 1 h / 0 °C

With hydrogen; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; hexane; ethyl acetate; toluene; 1.1: intermolecular Diels-Alder reaction;

DOI:10.1021/jo0610208

Reference yield:

(3R,4R)-4-acetyl-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-4-methylcyclohexan-1-one (862973-14-6) → (4S)-4-[(1R,2R)-5,5-dimethoxy-2-methyl-2-(1-propynyl)cyclohexyl]-2,2-dimethyl-1,3-dioxolane (862973-11-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 75 percent / PPTS / 2.5 h / 0 °C

2.1: KN(SiMe₃)2 / toluene; tetrahydrofuran / 1 h / -78 °C

3.1: LDA / tetrahydrofuran; hexane / 0.25 h / -78 °C

3.2: 435 mg / tetrahydrofuran; hexane / 1 h / 0 °C

With pyridinium p-toluenesulfonate; potassium hexamethylsilazane; lithium diisopropyl amide; In tetrahydrofuran; hexane; toluene;

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

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

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

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

Downstream raw materials:

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