di-(l)menthyl (1-mercaptobut-3-enyl)phosphonate

Base Information

• Chemical Name: di-(l)menthyl (1-mercaptobut-3-enyl)phosphonate
• CAS No.: 293329-47-2
• Molecular Formula: C₂₄H₄₅O₃PS
• Molecular Weight: 444.659
• Mol file: 293329-47-2.mol

Synonyms:di-(l)menthyl (1-mercaptobut-3-enyl)phosphonate

Chemical Property of di-(l)menthyl (1-mercaptobut-3-enyl)phosphonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of di-(l)menthyl (1-mercaptobut-3-enyl)phosphonate

There total 4 articles about di-(l)menthyl (1-mercaptobut-3-enyl)phosphonate 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:

di-(l)-menthyl (allylsulfanyl)methylphosphonate (293329-46-1) → ((R)-1-Mercapto-but-3-enyl)-phosphonic acid bis-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl) ester + di-(l)menthyl (1-mercaptobut-3-enyl)phosphonate (293329-47-2)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; In tetrahydrofuran; at -70 ℃; for 1.16667h; Title compound not separated from byproducts;

DOI:10.1080/10426509908546454

Reference yield:

hydrogen di[(1R,2S,5R)-menthyl] phosphite (211183-18-5) → di-(l)menthyl (1-mercaptobut-3-enyl)phosphonate (293329-47-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: potassium hydride / tetrahydrofuran / 3 h / 0 °C

1.2: tetrahydrofuran / 2 h / 20 °C

1.3: 82 percent / tetrahydrofuran / 20 °C

2.1: NaBH₄ / ethanol / 5 h / 0 - 70 °C

3.1: 95 percent / 20 °C

4.1: sec-BuLi; HMPA / tetrahydrofuran; cyclohexane / 1.25 h / -75 - -72 °C

4.2: HCl / H₂O

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; sec.-butyllithium; potassium hydride; In tetrahydrofuran; ethanol; cyclohexane; 1.1: Deprotonation / 1.2: Addition / 1.3: Methylation / 2.1: Reduction / 3.1: Addition / 4.1: Rearrangement / 4.2: Hydrolysis;

DOI:10.1021/ol005937j

Reference yield:

Mercaptomethyl-phosphonic acid bis-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl) ester → di-(l)menthyl (1-mercaptobut-3-enyl)phosphonate (293329-47-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 95 percent / 20 °C

2.1: sec-BuLi; HMPA / tetrahydrofuran; cyclohexane / 1.25 h / -75 - -72 °C

2.2: HCl / H₂O

With N,N,N,N,N,N-hexamethylphosphoric triamide; sec.-butyllithium; In tetrahydrofuran; cyclohexane; 1.1: Addition / 2.1: Rearrangement / 2.2: Hydrolysis;

DOI:10.1021/ol005937j

upstream raw materials:

di-(l)-menthyl (allylsulfanyl)methylphosphonate

hydrogen di[(1R,2S,5R)-menthyl] phosphite

S-methyl O,O-di-(-)-menthyl phosphonodithioformate