(2S,5S)-2-(tert-butyl)-5-(3-chlorophenyl)-5-heptyl-1,3-dioxolan-4-one

Base Information

• Chemical Name: (2S,5S)-2-(tert-butyl)-5-(3-chlorophenyl)-5-heptyl-1,3-dioxolan-4-one
• CAS No.: 1208232-04-5
• Molecular Formula: C₂₀H₂₉ClO₃
• Molecular Weight: 352.901
• Mol file: 1208232-04-5.mol

Synonyms:(2S,5S)-2-(tert-butyl)-5-(3-chlorophenyl)-5-heptyl-1,3-dioxolan-4-one

Chemical Property of (2S,5S)-2-(tert-butyl)-5-(3-chlorophenyl)-5-heptyl-1,3-dioxolan-4-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,5S)-2-(tert-butyl)-5-(3-chlorophenyl)-5-heptyl-1,3-dioxolan-4-one

There total 6 articles about (2S,5S)-2-(tert-butyl)-5-(3-chlorophenyl)-5-heptyl-1,3-dioxolan-4-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: 71.0%

1-Iodoheptane (4282-40-0) + (2S,5S)-2-(tert-butyl)-5-(3-chlorophenyl)-1,3-dioxolan-4-one (1208232-05-6) → (2S,5S)-2-(tert-butyl)-5-(3-chlorophenyl)-5-heptyl-1,3-dioxolan-4-one (1208232-04-5)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 3h; diastereoselective reaction; Inert atmosphere;

DOI:10.1016/j.bmc.2011.08.061

Reference yield:

(R)-3-chloromandelic acid methyl ester (153294-00-9) → (2S,5S)-2-(tert-butyl)-5-(3-chlorophenyl)-5-heptyl-1,3-dioxolan-4-one (1208232-04-5)

Guidance literature:

Multi-step reaction with 5 steps

1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

2: methanol; sodium azide / 1 h / 40 °C

3: water; sodium hydroxide / 40 °C

4: trifluorormethanesulfonic acid / pentane / 6 h / Reflux

5: N,N,N,N,N,N-hexamethylphosphoric triamide; lithium diisopropyl amide / tetrahydrofuran / 3 h / -78 °C / Inert atmosphere

With methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium azide; trifluorormethanesulfonic acid; water; triphenylphosphine; sodium hydroxide; lithium diisopropyl amide; diethylazodicarboxylate; In tetrahydrofuran; pentane;

DOI:10.1016/j.bmc.2011.08.061

Reference yield:

(R)-3-chloromandelic acid (16273-37-3,32222-43-8,52950-16-0,61008-98-8) → (2S,5S)-2-(tert-butyl)-5-(3-chlorophenyl)-5-heptyl-1,3-dioxolan-4-one (1208232-04-5)

Guidance literature:

Multi-step reaction with 6 steps

1: acetyl chloride / 20 °C

2: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

3: methanol; sodium azide / 1 h / 40 °C

4: water; sodium hydroxide / 40 °C

5: trifluorormethanesulfonic acid / pentane / 6 h / Reflux

6: N,N,N,N,N,N-hexamethylphosphoric triamide; lithium diisopropyl amide / tetrahydrofuran / 3 h / -78 °C / Inert atmosphere

With methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium azide; trifluorormethanesulfonic acid; water; acetyl chloride; triphenylphosphine; sodium hydroxide; lithium diisopropyl amide; diethylazodicarboxylate; In tetrahydrofuran; pentane;

DOI:10.1016/j.bmc.2011.08.061

upstream raw materials:

1-Iodoheptane

(2S,5S)-2-(tert-butyl)-5-(3-chlorophenyl)-1,3-dioxolan-4-one

(S)-2-(3-chlorophenyl)-2-hydroxyacetic acid

pivalaldehyde

Downstream raw materials:

(S)-(+)-2-(3-chlorophenyl)-2-hydroxynonanamide