Trifluoro-methanesulfonic acid (2R,4aR,9aS)-4a-methyl-2-phenyl-4a,8,9,9a-tetrahydro-4H-1,3,5-trioxa-benzocyclohepten-6-yl ester

Base Information

• Chemical Name: Trifluoro-methanesulfonic acid (2R,4aR,9aS)-4a-methyl-2-phenyl-4a,8,9,9a-tetrahydro-4H-1,3,5-trioxa-benzocyclohepten-6-yl ester
• CAS No.: 439265-00-6
• Molecular Formula: C₁₆H₁₇F₃O₆S
• Molecular Weight: 394.369
• Mol file: 439265-00-6.mol

Synonyms:Trifluoro-methanesulfonic acid (2R,4aR,9aS)-4a-methyl-2-phenyl-4a,8,9,9a-tetrahydro-4H-1,3,5-trioxa-benzocyclohepten-6-yl ester

Chemical Property of Trifluoro-methanesulfonic acid (2R,4aR,9aS)-4a-methyl-2-phenyl-4a,8,9,9a-tetrahydro-4H-1,3,5-trioxa-benzocyclohepten-6-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Trifluoro-methanesulfonic acid (2R,4aR,9aS)-4a-methyl-2-phenyl-4a,8,9,9a-tetrahydro-4H-1,3,5-trioxa-benzocyclohepten-6-yl ester

There total 5 articles about Trifluoro-methanesulfonic acid (2R,4aR,9aS)-4a-methyl-2-phenyl-4a,8,9,9a-tetrahydro-4H-1,3,5-trioxa-benzocyclohepten-6-yl 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:

(E)-4-((2R,4S,5R)-5-Hydroxy-2-phenyl-[1,3]dioxan-4-yl)-but-2-enoic acid methyl ester (250226-93-8) → Trifluoro-methanesulfonic acid (2R,4aR,9aS)-4a-methyl-2-phenyl-4a,8,9,9a-tetrahydro-4H-1,3,5-trioxa-benzocyclohepten-6-yl ester (439265-00-6)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 98 percent / H₂ / 5 percent Pd/C / ethyl acetate / 10 h / 20 °C

2.1: DMSO; (COCl)2 / CH₂Cl₂ / 1 h / -78 °C

2.2: Et₃N / CH₂Cl₂ / -78 - 20 °C

3.1: 742 mg / CH₂Cl₂; hexane / 2 h / -15 °C

4.1: LiOH*H₂O / tetrahydrofuran; H₂O / 1 h / 40 °C

5.1: Et₃N; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 °C

5.2: 1.97 g / DMAP / tetrahydrofuran; benzene / 1 h / 20 °C

6.1: DMPU; KHMDS / tetrahydrofuran; toluene / 0.5 h / -78 °C

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; lithium hydroxide; oxalyl dichloride; 2,4,6-trichlorobenzoyl chloride; hydrogen; potassium hexamethylsilazane; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; hexane; dichloromethane; water; ethyl acetate; toluene; 2.1: Swern oxidation / 5.1: Yamaguchi lactonization;

DOI:10.1016/S0040-4020(02)00039-X

Reference yield:

4-((2R,4S,5R)-5-Hydroxy-2-phenyl-[1,3]dioxan-4-yl)-butyric acid methyl ester (116237-17-3) → Trifluoro-methanesulfonic acid (2R,4aR,9aS)-4a-methyl-2-phenyl-4a,8,9,9a-tetrahydro-4H-1,3,5-trioxa-benzocyclohepten-6-yl ester (439265-00-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: DMSO; (COCl)2 / CH₂Cl₂ / 1 h / -78 °C

1.2: Et₃N / CH₂Cl₂ / -78 - 20 °C

2.1: 742 mg / CH₂Cl₂; hexane / 2 h / -15 °C

3.1: LiOH*H₂O / tetrahydrofuran; H₂O / 1 h / 40 °C

4.1: Et₃N; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 °C

4.2: 1.97 g / DMAP / tetrahydrofuran; benzene / 1 h / 20 °C

5.1: DMPU; KHMDS / tetrahydrofuran; toluene / 0.5 h / -78 °C

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; lithium hydroxide; oxalyl dichloride; 2,4,6-trichlorobenzoyl chloride; potassium hexamethylsilazane; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; hexane; dichloromethane; water; toluene; 1.1: Swern oxidation / 4.1: Yamaguchi lactonization;

DOI:10.1016/S0040-4020(02)00039-X

Reference yield:

4-((2R,4S,5R)-5-Hydroxy-5-methyl-2-phenyl-[1,3]dioxan-4-yl)-butyric acid methyl ester (370884-78-9) → Trifluoro-methanesulfonic acid (2R,4aR,9aS)-4a-methyl-2-phenyl-4a,8,9,9a-tetrahydro-4H-1,3,5-trioxa-benzocyclohepten-6-yl ester (439265-00-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: LiOH*H₂O / tetrahydrofuran; H₂O / 1 h / 40 °C

2.1: Et₃N; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 °C

2.2: 1.97 g / DMAP / tetrahydrofuran; benzene / 1 h / 20 °C

3.1: DMPU; KHMDS / tetrahydrofuran; toluene / 0.5 h / -78 °C

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; lithium hydroxide; 2,4,6-trichlorobenzoyl chloride; potassium hexamethylsilazane; triethylamine; In tetrahydrofuran; water; toluene; 2.1: Yamaguchi lactonization;

DOI:10.1016/S0040-4020(02)00039-X

upstream raw materials:

4-((2R,4S,5R)-5-Hydroxy-2-phenyl-[1,3]dioxan-4-yl)-butyric acid methyl ester

(E)-4-((2R,4S,5R)-5-Hydroxy-2-phenyl-[1,3]dioxan-4-yl)-but-2-enoic acid methyl ester

4-((2R,4S,5R)-5-Hydroxy-5-methyl-2-phenyl-[1,3]dioxan-4-yl)-butyric acid methyl ester

4-((2R,4S,5R)-5-Hydroxy-5-methyl-2-phenyl-[1,3]dioxan-4-yl)-butyric acid

Downstream raw materials:

3-((2R,4aR,9aS)-4a-Methyl-2-phenyl-4a,8,9,9a-tetrahydro-4H-1,3,5-trioxa-benzocyclohepten-6-yl)-propionic acid methyl ester

(2R,4aR,9aS)-4a-Methyl-2-phenyl-4a,8,9,9a-tetrahydro-4H-1,3,5-trioxa-benzocycloheptene-6-carboxylic acid methyl ester

((2R,4aR,9aS)-4a-Methyl-2-phenyl-4a,8,9,9a-tetrahydro-4H-1,3,5-trioxa-benzocyclohepten-6-yl)-methanol

(2R,4aR,9aS)-6-(4-Methoxy-benzyloxymethyl)-4a-methyl-2-phenyl-4a,8,9,9a-tetrahydro-4H-1,3,5-trioxa-benzocycloheptene