(3S,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-fluoro-dihydro-thiophen-2-one

Base Information

• Chemical Name: (3S,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-fluoro-dihydro-thiophen-2-one
• CAS No.: 476210-45-4
• Molecular Formula: C₂₁H₂₅FO₂SSi
• Molecular Weight: 388.578
• Mol file: 476210-45-4.mol

Synonyms:(3S,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-fluoro-dihydro-thiophen-2-one

Chemical Property of (3S,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-fluoro-dihydro-thiophen-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-fluoro-dihydro-thiophen-2-one

There total 7 articles about (3S,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-fluoro-dihydro-thiophen-2-one 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:

5-(tert-butyl-diphenyl-silanyloxymethyl)-3-fluoro-5H-furan-2-one → (3S,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-fluoro-dihydro-thiophen-2-one (476210-45-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: H₂ / Pd/C

2.1: NaOH

3.1: I₂; PPh₃; imidazole

4.1: dimethylformamide

5.1: DIBAL-H

5.2: acetic anhydride / dimethylsulfoxide

With 1H-imidazole; sodium hydroxide; hydrogen; iodine; diisobutylaluminium hydride; triphenylphosphine; palladium on activated charcoal; In N,N-dimethyl-formamide;

DOI:10.1081/NCN-120021965

Reference yield:

5-(tert-butyldiphenylsilyloxy)-2-fluoro-4-iodopentanoic acid methyl ester (476209-86-6) → (3S,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-fluoro-dihydro-thiophen-2-one (476210-45-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: dimethylformamide

2.1: DIBAL-H

2.2: acetic anhydride / dimethylsulfoxide

With diisobutylaluminium hydride; In N,N-dimethyl-formamide;

DOI:10.1081/NCN-120021965

Reference yield:

(2S,4S)-5-(tert-Butyl-diphenyl-silanyloxy)-2-fluoro-4-hydroxy-pentanoic acid methyl ester (1028289-72-6) → (3S,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-fluoro-dihydro-thiophen-2-one (476210-45-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 7.52 g / I₂; imidazole; PPh₃ / toluene / 4 h / 60 °C

2: 87 percent / dimethylformamide / 8 h / 20 °C

3: DIBAL-H / toluene; hexane / 1 h / -78 °C

4: Ac₂O; DMSO / 24 h / 20 °C

With 1H-imidazole; iodine; acetic anhydride; diisobutylaluminium hydride; dimethyl sulfoxide; triphenylphosphine; In hexane; N,N-dimethyl-formamide; toluene; 4: Moffat-type oxidation;

DOI:10.1021/jm020246+

upstream raw materials:

4-(acetylsulfanyl)-5-(tert-butyldiphenylsilyloxy)-2-fluoropentanoic acid methyl ester

5-(tert-butyldiphenylsilyloxy)-2-fluoro-4-iodopentanoic acid methyl ester

(2S,4S)-5-(tert-Butyl-diphenyl-silanyloxy)-2-fluoro-4-hydroxy-pentanoic acid methyl ester

Downstream raw materials:

(2S,4R)-(-)-4-tert-butyldiphenylsilyloxymethyl-2-fluoro-2-phenylselenyl-γ-thiobutyrolactone