(R)-benzyl 4-(1-(1H-imidazole-1(R/S)-carbonothioyloxy)-3-ethoxy-2,2-difluoro-3-oxopropyl)-2,2-dimethyloxazolidine-3-carboxylate

Base Information

• Chemical Name: (R)-benzyl 4-(1-(1H-imidazole-1(R/S)-carbonothioyloxy)-3-ethoxy-2,2-difluoro-3-oxopropyl)-2,2-dimethyloxazolidine-3-carboxylate
• CAS No.: 510713-90-3
• Molecular Formula: C₂₂H₂₅F₂N₃O₆S
• Molecular Weight: 497.52
• Mol file: 510713-90-3.mol

Synonyms:(R)-benzyl 4-(1-(1H-imidazole-1(R/S)-carbonothioyloxy)-3-ethoxy-2,2-difluoro-3-oxopropyl)-2,2-dimethyloxazolidine-3-carboxylate

Chemical Property of (R)-benzyl 4-(1-(1H-imidazole-1(R/S)-carbonothioyloxy)-3-ethoxy-2,2-difluoro-3-oxopropyl)-2,2-dimethyloxazolidine-3-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-benzyl 4-(1-(1H-imidazole-1(R/S)-carbonothioyloxy)-3-ethoxy-2,2-difluoro-3-oxopropyl)-2,2-dimethyloxazolidine-3-carboxylate

There total 6 articles about (R)-benzyl 4-(1-(1H-imidazole-1(R/S)-carbonothioyloxy)-3-ethoxy-2,2-difluoro-3-oxopropyl)-2,2-dimethyloxazolidine-3-carboxylate 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:

1,1'-Thiocarbonyldiimidazole (6160-65-2) + (4R)-4-[(1RS)-2-ethoxycarbonyl-2,2-difluoro1-hydroxyethyl]-2,2-dimethyloxazolidine-3-carboxylic acid benzyl ester (510713-88-9) → (R)-benzyl 4-(1-(1H-imidazole-1(R/S)-carbonothioyloxy)-3-ethoxy-2,2-difluoro-3-oxopropyl)-2,2-dimethyloxazolidine-3-carboxylate (510713-90-3)

Guidance literature:

In tetrahydrofuran; at 30 - 40 ℃; for 48h;

DOI:10.1055/s-2002-35616

Reference yield:

(R)-methyl 2-(((benzyloxy)carbonyl)amino)-3-hydroxypropanoate (93204-36-5) → (R)-benzyl 4-(1-(1H-imidazole-1(R/S)-carbonothioyloxy)-3-ethoxy-2,2-difluoro-3-oxopropyl)-2,2-dimethyloxazolidine-3-carboxylate (510713-90-3)

Guidance literature:

Multi-step reaction with 5 steps

1: BF₃*Et₂O / acetone

2: NaBH₄ / tetrahydrofuran; methanol

3: 87 percent / aq. NaClO; TEMPO; NaBr / ethyl acetate; toluene / 0.25 h / 0 °C

4: 79 percent / Zn / tetrahydrofuran / 0.25 h / Heating

5: tetrahydrofuran / 48 h / 30 - 40 °C

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium tetrahydroborate; boron trifluoride diethyl etherate; sodium bromide; zinc; In tetrahydrofuran; methanol; ethyl acetate; acetone; toluene; 4: Reformatsky reaction;

DOI:10.1055/s-2002-35616

Reference yield:

(4R)-4-formyl-2,2-dimethyloxazolidine-3-carboxylic acid benzyl ester (133464-37-6) → (R)-benzyl 4-(1-(1H-imidazole-1(R/S)-carbonothioyloxy)-3-ethoxy-2,2-difluoro-3-oxopropyl)-2,2-dimethyloxazolidine-3-carboxylate (510713-90-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 79 percent / Zn / tetrahydrofuran / 0.25 h / Heating

2: tetrahydrofuran / 48 h / 30 - 40 °C

With zinc; In tetrahydrofuran; 1: Reformatsky reaction;

DOI:10.1055/s-2002-35616

upstream raw materials:

1,1'-Thiocarbonyldiimidazole

(4R)-4-[(1RS)-2-ethoxycarbonyl-2,2-difluoro1-hydroxyethyl]-2,2-dimethyloxazolidine-3-carboxylic acid benzyl ester

(R)-methyl 2-(((benzyloxy)carbonyl)amino)-3-hydroxypropanoate

(4R)-4-formyl-2,2-dimethyloxazolidine-3-carboxylic acid benzyl ester

Downstream raw materials:

2-(2-tert-butoxycarbonylamino-benzoylamino)-4-{1-tert-butoxycarbonyl-3-[1-tert-butoxycarbonyl-2-(4-hydroxy-3-nitro-phenyl)-ethylcarbamoyl]-propylcarbamoyl}-4,4-difluoro-butyric acid tert-butyl ester

N-Boc-Abz-4,4-difluoroglutamic acid α-tert-butyl ester γ-glutamic acid α-tert-butyl γ-2-(trimethylsilyl)ethyl ester

N-Cbz-(2S)-4,4-difluoroglutamic acid α-tert-butyl ester γ-glutamic acid α-tert-butyl γ-2-(trimethylsilyl)ethyl ester

N-Cbz-difluorooxazolidine-γ-L-glutamic acid α-tert-butyl ester γ-(2-trimethylsilyl)ethyl ester