(R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (5S,6R)-3-acetoxy-6-methanesulfonyloxy-5-methyl-heptyl ester

Base Information

• Chemical Name: (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (5S,6R)-3-acetoxy-6-methanesulfonyloxy-5-methyl-heptyl ester
• CAS No.: 325959-96-4
• Molecular Formula: C₂₁H₂₉F₃O₈S
• Molecular Weight: 498.518
• Mol file: 325959-96-4.mol

Synonyms:(R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (5S,6R)-3-acetoxy-6-methanesulfonyloxy-5-methyl-heptyl ester

Chemical Property of (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (5S,6R)-3-acetoxy-6-methanesulfonyloxy-5-methyl-heptyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (5S,6R)-3-acetoxy-6-methanesulfonyloxy-5-methyl-heptyl ester

There total 8 articles about (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (5S,6R)-3-acetoxy-6-methanesulfonyloxy-5-methyl-heptyl 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:

(3S,4R)-3-Methyl-4-(2-trimethylsilanyl-ethoxymethoxy)-pentanal → (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (5S,6R)-3-acetoxy-6-methanesulfonyloxy-5-methyl-heptyl ester (325959-96-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 315 mg / diethyl ether / 14 h / 20 °C

2.1: 273 mg / pyridine / 6 h / 20 °C

3.1: OsO₄; 4-methylmorpholine N-oxide / 22; 3 / acetonitrile / 64 h / 20 °C

3.2: NaIO₄ / tetrahydrofuran; aq. phosphate buffer / 1 h / 0 °C / pH 7.0

3.3: 13 mg / NaBH₄ / ethanol / 1 h / 0 °C

4.1: DMAP; Et₃N / CH₂Cl₂ / 3 h / 20 °C

5.1: TFA / CH₂Cl₂ / 1 h / 0 °C

6.1: 40.1 mg / DMAD; Et₃N / CH₂Cl₂ / 4 h / 0 °C

With pyridine; dmap; osmium(VIII) oxide; 4-methylmorpholine N-oxide; triethylamine; trifluoroacetic acid; 22; 3; In diethyl ether; dichloromethane; acetonitrile; 1.1: Grignard reaction;

DOI:10.1021/jo005607c

Reference yield:

(2R,3R)-1-iodo-2-methyl-3-[2-(trimethylsilyl)ethoxymethoxy]butane → (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (5S,6R)-3-acetoxy-6-methanesulfonyloxy-5-methyl-heptyl ester (325959-96-4)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 359 mg / dimethylsulfoxide / 4 h / 70 °C

2.1: 336 mg / DIBAL / hexane / 1 h / -78 °C

3.1: 315 mg / diethyl ether / 14 h / 20 °C

4.1: 273 mg / pyridine / 6 h / 20 °C

5.1: OsO₄; 4-methylmorpholine N-oxide / 22; 3 / acetonitrile / 64 h / 20 °C

5.2: NaIO₄ / tetrahydrofuran; aq. phosphate buffer / 1 h / 0 °C / pH 7.0

5.3: 13 mg / NaBH₄ / ethanol / 1 h / 0 °C

6.1: DMAP; Et₃N / CH₂Cl₂ / 3 h / 20 °C

7.1: TFA / CH₂Cl₂ / 1 h / 0 °C

8.1: 40.1 mg / DMAD; Et₃N / CH₂Cl₂ / 4 h / 0 °C

With pyridine; dmap; osmium(VIII) oxide; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; triethylamine; trifluoroacetic acid; 22; 3; In diethyl ether; hexane; dichloromethane; dimethyl sulfoxide; acetonitrile; 3.1: Grignard reaction;

DOI:10.1021/jo005607c

Reference yield:

(3S,4R)-3-Methyl-4-(2-trimethylsilanyl-ethoxymethoxy)-pentanenitrile → (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (5S,6R)-3-acetoxy-6-methanesulfonyloxy-5-methyl-heptyl ester (325959-96-4)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 336 mg / DIBAL / hexane / 1 h / -78 °C

2.1: 315 mg / diethyl ether / 14 h / 20 °C

3.1: 273 mg / pyridine / 6 h / 20 °C

4.1: OsO₄; 4-methylmorpholine N-oxide / 22; 3 / acetonitrile / 64 h / 20 °C

4.2: NaIO₄ / tetrahydrofuran; aq. phosphate buffer / 1 h / 0 °C / pH 7.0

4.3: 13 mg / NaBH₄ / ethanol / 1 h / 0 °C

5.1: DMAP; Et₃N / CH₂Cl₂ / 3 h / 20 °C

6.1: TFA / CH₂Cl₂ / 1 h / 0 °C

7.1: 40.1 mg / DMAD; Et₃N / CH₂Cl₂ / 4 h / 0 °C

With pyridine; dmap; osmium(VIII) oxide; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; triethylamine; trifluoroacetic acid; 22; 3; In diethyl ether; hexane; dichloromethane; acetonitrile; 2.1: Grignard reaction;

DOI:10.1021/jo005607c

upstream raw materials:

methanesulfonyl chloride

(2R,3S,5RS)-5-acetyloxy-3-methyl-2-[2-(trimethylsilyl)ethoxymethoxy]oct-7-ene

(2R,3S,5RS)-5-acetyloxy-3-methyl-2-[2-(trimethylsilyl)ethoxymethoxy]heptan-7-ol