methyl (R)-(+)-5-(cyclohex-1-en-1-yl)-4-[(diethoxyphosphoryl)oxy]pent-2-ynoate

Base Information

• Chemical Name: methyl (R)-(+)-5-(cyclohex-1-en-1-yl)-4-[(diethoxyphosphoryl)oxy]pent-2-ynoate
• CAS No.: 190787-38-3
• Molecular Formula: C₁₆H₂₅O₆P
• Molecular Weight: 344.345
• Mol file: 190787-38-3.mol

Synonyms:methyl (R)-(+)-5-(cyclohex-1-en-1-yl)-4-[(diethoxyphosphoryl)oxy]pent-2-ynoate

Chemical Property of methyl (R)-(+)-5-(cyclohex-1-en-1-yl)-4-[(diethoxyphosphoryl)oxy]pent-2-ynoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (R)-(+)-5-(cyclohex-1-en-1-yl)-4-[(diethoxyphosphoryl)oxy]pent-2-ynoate

There total 4 articles about methyl (R)-(+)-5-(cyclohex-1-en-1-yl)-4-[(diethoxyphosphoryl)oxy]pent-2-ynoate 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:

methyl 3-formylpropiolate (124598-37-4) → methyl (R)-(+)-5-(cyclohex-1-en-1-yl)-4-[(diethoxyphosphoryl)oxy]pent-2-ynoate (190787-38-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: (R)-binaphthol-titanium dichloride / CH₂Cl₂ / 0 °C

2.1: butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C

2.2: Et₃N / tetrahydrofuran; hexane / 1 h / 0 °C

With n-butyllithium; (R)-binaphthol-titanium dichloride ((R)-BINOL-TiCl₂); In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1016/S0040-4020(00)01044-9

Reference yield:

methylenecyclohexane (1192-37-6) → methyl (R)-(+)-5-(cyclohex-1-en-1-yl)-4-[(diethoxyphosphoryl)oxy]pent-2-ynoate (190787-38-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: (R)-binaphthol-titanium dichloride / CH₂Cl₂ / 0 °C

2.1: butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C

2.2: Et₃N / tetrahydrofuran; hexane / 1 h / 0 °C

With n-butyllithium; (R)-binaphthol-titanium dichloride ((R)-BINOL-TiCl₂); In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1016/S0040-4020(00)01044-9

Reference yield:

diethyl chlorophosphate (814-49-3) + methyl (R)-(+)-5-(cyclohex-1-en-1-yl)-4-hydroxypent-2-ynoate (185397-10-8) → (S)-5-Cyclohex-1-enyl-4-(diethoxy-phosphoryloxy)-pent-2-ynoic acid methyl ester + methyl (R)-(+)-5-(cyclohex-1-en-1-yl)-4-[(diethoxyphosphoryl)oxy]pent-2-ynoate (190787-38-3)

Guidance literature:

methyl (R)-(+)-5-(cyclohex-1-en-1-yl)-4-hydroxypent-2-ynoate; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1h;

diethyl chlorophosphate; With triethylamine; In tetrahydrofuran; hexane; at 0 ℃; for 1h; Title compound not separated from byproducts;

DOI:10.1016/S0040-4020(00)01044-9

upstream raw materials:

diethyl chlorophosphate

methyl (R)-(+)-5-(cyclohex-1-en-1-yl)-4-hydroxypent-2-ynoate

methyl 3-formylpropiolate

methylenecyclohexane