(1R,2R)-(5E)-2-isopropenyl-5-methyl-5-cyclodecen-9-ynyl (S)-O-methylmandelate

Base Information

• Chemical Name: (1R,2R)-(5E)-2-isopropenyl-5-methyl-5-cyclodecen-9-ynyl (S)-O-methylmandelate
• CAS No.: 113680-90-3
• Molecular Formula: C₂₃H₂₈O₃
• Molecular Weight: 352.474
• Mol file: 113680-90-3.mol

Synonyms:(1R,2R)-(5E)-2-isopropenyl-5-methyl-5-cyclodecen-9-ynyl (S)-O-methylmandelate

Chemical Property of (1R,2R)-(5E)-2-isopropenyl-5-methyl-5-cyclodecen-9-ynyl (S)-O-methylmandelate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2R)-(5E)-2-isopropenyl-5-methyl-5-cyclodecen-9-ynyl (S)-O-methylmandelate

There total 1 articles about (1R,2R)-(5E)-2-isopropenyl-5-methyl-5-cyclodecen-9-ynyl (S)-O-methylmandelate 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%

(S)-2-methoxy-2-phenylacetic acid (26164-26-1) + (+)-(1R,2R)-(5E)-2-isopropenyl-5-methyl-5-cyclodecen-9-yn-1-ol (113725-52-3) → (1R,2R)-(5E)-2-isopropenyl-5-methyl-5-cyclodecen-9-ynyl (S)-O-methylmandelate (113680-90-3)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; Ambient temperature;

DOI:10.1021/ja00217a039

Reference yield:

(1R,2R)-(5E)-2-isopropenyl-5-methyl-5-cyclodecen-9-ynyl (S)-O-methylmandelate (113680-90-3) → Benzoic acid (E)-(1S,10R)-10-isopropenyl-7-methyl-cyclodec-6-en-2-ynyl ester

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent / KOH / methanol / 0.75 h / Ambient temperature

2: triphenylphosphine,DEAD / benzene / 8 h / Ambient temperature

With potassium hydroxide; triphenylphosphine; diethylazodicarboxylate; In methanol; benzene;

DOI:10.1021/ja00217a039

Reference yield:

(1R,2R)-(5E)-2-isopropenyl-5-methyl-5-cyclodecen-9-ynyl (S)-O-methylmandelate (113680-90-3) → aristolactone (6790-85-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 70 percent / KOH / methanol / 0.75 h / Ambient temperature

2: triphenylphosphine,DEAD / benzene / 8 h / Ambient temperature

3: 55 mg / KOH / methanol / 1.5 h / Ambient temperature

4: Red-Al / tetrahydrofuran

5: N-iodosuccinimide / tetrahydrofuran

6: 12 mg / hydrazine, K₂CO₃ / (Ph₃P)2PdCl₂ / tetrahydrofuran / 10 h / 35 °C / 4137.2 Torr

With potassium hydroxide; N-iodo-succinimide; potassium carbonate; triphenylphosphine; sodium bis(2-methoxyethoxy)aluminium dihydride; hydrazine; diethylazodicarboxylate; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; methanol; benzene;

DOI:10.1021/ja00217a039

upstream raw materials:

(S)-2-methoxy-2-phenylacetic acid

(+)-(1R,2R)-(5E)-2-isopropenyl-5-methyl-5-cyclodecen-9-yn-1-ol

Downstream raw materials:

aristolactone