(Z)-(R)-8-Benzyloxy-6-methanesulfonyloxy-oct-2-enoic acid ethyl ester

Base Information

• Chemical Name: (Z)-(R)-8-Benzyloxy-6-methanesulfonyloxy-oct-2-enoic acid ethyl ester
• CAS No.: 869348-31-2
• Molecular Formula: C₁₈H₂₆O₆S
• Molecular Weight: 370.467
• Mol file: 869348-31-2.mol

Synonyms:(Z)-(R)-8-Benzyloxy-6-methanesulfonyloxy-oct-2-enoic acid ethyl ester

Chemical Property of (Z)-(R)-8-Benzyloxy-6-methanesulfonyloxy-oct-2-enoic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-(R)-8-Benzyloxy-6-methanesulfonyloxy-oct-2-enoic acid ethyl ester

There total 6 articles about (Z)-(R)-8-Benzyloxy-6-methanesulfonyloxy-oct-2-enoic acid ethyl ester 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:

ethyl (R,Z)-8-benzyloxy-6-hydroxy-2-octenoate (869348-30-1) + methanesulfonyl chloride (124-63-0) → (Z)-(R)-8-Benzyloxy-6-methanesulfonyloxy-oct-2-enoic acid ethyl ester (869348-31-2)

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃;

DOI:10.1021/ol051507n

Reference yield:

(R)-1-benzyloxy-6-hepten-3-ol (869348-19-6) → (Z)-(R)-8-Benzyloxy-6-methanesulfonyloxy-oct-2-enoic acid ethyl ester (869348-31-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 86 percent / imidazole; TBAI / dimethylformamide / 1 h

2.1: ozone / CH₂Cl₂ / -78 °C

2.2: 70 percent / PPh₃ / CH₂Cl₂ / 0.5 h / 20 °C

3.1: 18-crown-6; KHMDS / tetrahydrofuran; toluene / 1 h / -78 °C

4.1: aq. HCl / methanol / 0.08 h

5.1: Et₃N / CH₂Cl₂ / 0 °C

With 1H-imidazole; hydrogenchloride; 18-crown-6 ether; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; ozone; triethylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ol051507n

Reference yield:

(R)-6-benzyloxy-4-(triethylsilyloxy)hexanal (869348-28-7) → (Z)-(R)-8-Benzyloxy-6-methanesulfonyloxy-oct-2-enoic acid ethyl ester (869348-31-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 18-crown-6; KHMDS / tetrahydrofuran; toluene / 1 h / -78 °C

2: aq. HCl / methanol / 0.08 h

3: Et₃N / CH₂Cl₂ / 0 °C

With hydrogenchloride; 18-crown-6 ether; potassium hexamethylsilazane; triethylamine; In tetrahydrofuran; methanol; dichloromethane; toluene;

DOI:10.1021/ol051507n

upstream raw materials:

ethyl (R,Z)-8-benzyloxy-6-hydroxy-2-octenoate

methanesulfonyl chloride

(R)-1-benzyloxy-6-hepten-3-ol

(R)-6-benzyloxy-4-(triethylsilyloxy)hexanal