(R)-1-Benzyloxy-4-{(S)-2-[2-((E)-(R)-4-bromo-2-triisopropylsilanyloxy-pent-3-enyl)-thiazol-4-yl]-propyl}-azetidin-2-one

Base Information

• Chemical Name: (R)-1-Benzyloxy-4-{(S)-2-[2-((E)-(R)-4-bromo-2-triisopropylsilanyloxy-pent-3-enyl)-thiazol-4-yl]-propyl}-azetidin-2-one
• CAS No.: 201340-05-8
• Molecular Formula: C₃₀H₄₅BrN₂O₃SSi
• Molecular Weight: 621.754
• Mol file: 201340-05-8.mol

Synonyms:(R)-1-Benzyloxy-4-{(S)-2-[2-((E)-(R)-4-bromo-2-triisopropylsilanyloxy-pent-3-enyl)-thiazol-4-yl]-propyl}-azetidin-2-one

Chemical Property of (R)-1-Benzyloxy-4-{(S)-2-[2-((E)-(R)-4-bromo-2-triisopropylsilanyloxy-pent-3-enyl)-thiazol-4-yl]-propyl}-azetidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-1-Benzyloxy-4-{(S)-2-[2-((E)-(R)-4-bromo-2-triisopropylsilanyloxy-pent-3-enyl)-thiazol-4-yl]-propyl}-azetidin-2-one

There total 17 articles about (R)-1-Benzyloxy-4-{(S)-2-[2-((E)-(R)-4-bromo-2-triisopropylsilanyloxy-pent-3-enyl)-thiazol-4-yl]-propyl}-azetidin-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: 92.0%

(Z)-(S)-5-[2-((E)-(R)-4-Bromo-2-triisopropylsilanyloxy-pent-3-enyl)-thiazol-4-yl]-3-hydroxy-hex-2-enoic acid benzyloxy-amide → (R)-1-Benzyloxy-4-{(S)-2-[2-((E)-(R)-4-bromo-2-triisopropylsilanyloxy-pent-3-enyl)-thiazol-4-yl]-propyl}-azetidin-2-one (201340-05-8)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 25 ℃;

DOI:10.1021/ja973549f

Reference yield: 92.0%

(3S,5S)-5-[2-((E)-(R)-4-Bromo-2-triisopropylsilanyloxy-pent-3-enyl)-thiazol-4-yl]-3-hydroxy-hexanoic acid benzyloxy-amide (218782-77-5) → (R)-1-Benzyloxy-4-{(S)-2-[2-((E)-(R)-4-bromo-2-triisopropylsilanyloxy-pent-3-enyl)-thiazol-4-yl]-propyl}-azetidin-2-one (201340-05-8)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 25 ℃; for 2.5h;

DOI:10.1021/ja981846u

Reference yield:

(E)-(R)-5-Bromo-3-hydroxy-1-((S)-4-isopropyl-2-thioxo-thiazolidin-3-yl)-hex-4-en-1-one (218782-63-9) → (R)-1-Benzyloxy-4-{(S)-2-[2-((E)-(R)-4-bromo-2-triisopropylsilanyloxy-pent-3-enyl)-thiazol-4-yl]-propyl}-azetidin-2-one (201340-05-8)

Guidance literature:

Multi-step reaction with 13 steps

1: 99 percent / 2,6-lutidine / CH₂Cl₂ / 0.67 h / 0 - 20 °C

2: 90 percent / NH₃ gas / CH₂Cl₂ / 0 °C

3: 72 percent / (PhOPh)2P₂S₄ / tetrahydrofuran / 0.5 h / 25 °C

4: KHCO₃ / 1,2-dimethoxy-ethane / -30 - 25 °C

5: trifluoroacetic anhydride, 2,6-lutidine / 1,2-dimethoxy-ethane / 1 h / -30 °C

6: 80 percent / DIBAL-H / CH₂Cl₂ / 3 h / -90 °C

7: 1.) NaHMDS / 1.) THF, 25 deg C, 15 min, 2.) THF, 25 deg C, 1.5 h

8: 1.) CuBr*DMS / 1.) THF, Et₂O, from -78 to 0 deg C, 30 min, 2.) THF, Et₂O, CH₂Cl₂, -30 deg C, 3.5 h

9: 1.) AlMe₃ / 1.) CH₂Cl₂, toluene, 25 deg C, 30 min, 2.) CH₂Cl₂, toluene, -20 deg C, 8 h

10: 95 percent / DIBAL-H / tetrahydrofuran; CH₂Cl₂ / 1.3 h / -78 °C

11: 1.) Sn(OTf)2, N-ethylpiperidine / 1.) CH₂Cl₂, -50 deg C, 4 h, 2.) CH₂Cl₂, -78 deg C, 1 h

12: 1.) Et₃N / 1.) CH₂Cl₂, 25 deg C, 30 min, 2.) CH₂Cl₂, RT, 27 h

13: 92 percent / diisopropylazodicarboxylate, Ph₃P / tetrahydrofuran / 2.5 h / 25 °C

With 1-ethyl-piperidine; 2,6-dimethylpyridine; tin(II) trifluoromethanesulfonate; copper(I) bromide dimethylsulfide complex; di-isopropyl azodicarboxylate; (PhOPh)2P₂S₄; ammonia; trimethylaluminum; sodium hexamethyldisilazane; diisobutylaluminium hydride; potassium hydrogencarbonate; triethylamine; triphenylphosphine; trifluoroacetic anhydride; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane;

DOI:10.1021/ja981846u

upstream raw materials:

(3S,5S)-5-[2-((E)-(R)-4-Bromo-2-triisopropylsilanyloxy-pent-3-enyl)-thiazol-4-yl]-3-hydroxy-hexanoic acid benzyloxy-amide

(E)-(R)-5-Bromo-3-triisopropylsilanyloxy-hex-4-enoic acid amide

(E)-(R)-5-Bromo-3-triisopropylsilanyloxy-hex-4-enethioic acid amide

(E)-(R)-5-Bromo-3-hydroxy-1-((S)-4-isopropyl-2-thioxo-thiazolidin-3-yl)-hex-4-en-1-one

Downstream raw materials:

(-)-pateamine