2-[2-((4S,5S)-5-Hexyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-phenylsulfanyl-ethyl]-3-hydroxy-cyclohex-2-enone

Base Information

• Chemical Name: 2-[2-((4S,5S)-5-Hexyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-phenylsulfanyl-ethyl]-3-hydroxy-cyclohex-2-enone
• CAS No.: 244071-57-6
• Molecular Formula: C₂₅H₃₆O₄S
• Molecular Weight: 432.624
• Mol file: 244071-57-6.mol

Synonyms:2-[2-((4S,5S)-5-Hexyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-phenylsulfanyl-ethyl]-3-hydroxy-cyclohex-2-enone

Chemical Property of 2-[2-((4S,5S)-5-Hexyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-phenylsulfanyl-ethyl]-3-hydroxy-cyclohex-2-enone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[2-((4S,5S)-5-Hexyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-phenylsulfanyl-ethyl]-3-hydroxy-cyclohex-2-enone

There total 5 articles about 2-[2-((4S,5S)-5-Hexyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-phenylsulfanyl-ethyl]-3-hydroxy-cyclohex-2-enone 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: 77.8%

1,3-cylohexanedione (504-02-9) + thiophenol (108-98-5) + ((4S,5S)-5-hexyl-2,2-dimethyl[1,3]dioxolan-4-yl)acetaldehyde (244071-54-3) → 2-[2-((4S,5S)-5-Hexyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-phenylsulfanyl-ethyl]-3-hydroxy-cyclohex-2-enone (244071-57-6) + (4S,5S)-4-[2,2-bis(1-hydroxyl-3-oxocyclohexen-2-yl)ethyl]-5-hexyl-2,2-dimethyl[1,3]dioxolane

Guidance literature:

With silica gel; In dichloromethane; at 30 - 35 ℃;

DOI:10.1039/a901320b

Reference yield:

2,3-O-isopropylidene-L-threitol (50622-09-8) → 2-[2-((4S,5S)-5-Hexyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-phenylsulfanyl-ethyl]-3-hydroxy-cyclohex-2-enone (244071-57-6)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 85 percent / Et₃N / CH₂Cl₂ / 4 h / 20 °C

2.1: 51 percent / Li₂Cu₂Cl₄ / tetrahydrofuran / 10 h / 20 °C

3.1: 95 percent / NaI / dimethylformamide / 2 h / 80 - 90 °C

4.1: 85 percent / CuI / tetrahydrofuran; hexamethylphosphoric acid triamide / 5 h / 20 °C

5.1: O₃ / methanol; CH₂Cl₂ / -78 °C

5.2: 90 percent / Me₂S / methanol; CH₂Cl₂ / 20 °C

6.1: 40 percent / SiO₂ / CH₂Cl₂ / 48 h / 30 - 35 °C

With copper(l) iodide; 2Li⁽¹⁺⁾*Cl₄Cu₂^(2-); silica gel; ozone; triethylamine; sodium iodide; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1055/s-2001-9741

Reference yield:

(4S,5S)-2,2-dimethyl-4,5-bis(p-toluenesulfonyloxymethyl)-1,3-dioxolan (37002-45-2) → 2-[2-((4S,5S)-5-Hexyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-phenylsulfanyl-ethyl]-3-hydroxy-cyclohex-2-enone (244071-57-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 51 percent / Li₂Cu₂Cl₄ / tetrahydrofuran / 10 h / 20 °C

2.1: 95 percent / NaI / dimethylformamide / 2 h / 80 - 90 °C

3.1: 85 percent / CuI / tetrahydrofuran; hexamethylphosphoric acid triamide / 5 h / 20 °C

4.1: O₃ / methanol; CH₂Cl₂ / -78 °C

4.2: 90 percent / Me₂S / methanol; CH₂Cl₂ / 20 °C

5.1: 40 percent / SiO₂ / CH₂Cl₂ / 48 h / 30 - 35 °C

With copper(l) iodide; 2Li⁽¹⁺⁾*Cl₄Cu₂^(2-); silica gel; ozone; sodium iodide; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1055/s-2001-9741

upstream raw materials:

1,3-cylohexanedione

thiophenol

((4S,5S)-5-hexyl-2,2-dimethyl[1,3]dioxolan-4-yl)acetaldehyde

2,3-O-isopropylidene-L-threitol

Downstream raw materials:

(S)-2-((S)-1-Hydroxy-heptyl)-4-phenylsulfanyl-2,3,4,6,7,8-hexahydro-chromen-5-one

2-[2-((4S,5S)-5-Hexyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl]-3-hydroxy-cyclohex-2-enone