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

Base Information

• Chemical Name: (3S,5S)-5-[2-((E)-(R)-4-Bromo-2-triisopropylsilanyloxy-pent-3-enyl)-thiazol-4-yl]-3-hydroxy-hexanoic acid benzyloxy-amide
• CAS No.: 218782-77-5
• Molecular Formula: C₃₀H₄₇BrN₂O₄SSi
• Molecular Weight: 639.77
• Mol file: 218782-77-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 12 articles about (3S,5S)-5-[2-((E)-(R)-4-Bromo-2-triisopropylsilanyloxy-pent-3-enyl)-thiazol-4-yl]-3-hydroxy-hexanoic acid benzyloxy-amide 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)-(R)-5-Bromo-3-triisopropylsilanyloxy-hex-4-enethioic acid amide (218782-66-2) → (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)

Guidance literature:

Multi-step reaction with 9 steps

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

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

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

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

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

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

7: 95 percent / DIBAL-H / tetrahydrofuran; CH₂Cl₂ / 1.3 h / -78 °C

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

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

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

DOI:10.1021/ja981846u

Reference yield:

(E)-(R)-5-Bromo-3-triisopropylsilanyloxy-hex-4-enoic acid amide (201339-99-3) → (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)

Guidance literature:

Multi-step reaction with 10 steps

1: 72 percent / (PhOPh)2P₂S₄ / tetrahydrofuran / 0.5 h / 25 °C

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

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

4: 80 percent / DIBAL-H / CH₂Cl₂ / 3 h / -90 °C

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

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

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

8: 95 percent / DIBAL-H / tetrahydrofuran; CH₂Cl₂ / 1.3 h / -78 °C

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

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

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

DOI:10.1021/ja981846u

Reference yield:

2-((E)-(R)-4-Bromo-2-triisopropylsilanyloxy-pent-3-enyl)-thiazole-4-carbaldehyde (201340-01-4) → (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)

Guidance literature:

Multi-step reaction with 6 steps

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

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

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

4: 95 percent / DIBAL-H / tetrahydrofuran; CH₂Cl₂ / 1.3 h / -78 °C

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

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

With 1-ethyl-piperidine; tin(II) trifluoromethanesulfonate; copper(I) bromide dimethylsulfide complex; trimethylaluminum; sodium hexamethyldisilazane; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja981846u

upstream raw materials:

O-benzylhydoxylamine hydrochloride

(3S,5S)-5-[2-((E)-(R)-4-Bromo-2-triisopropylsilanyloxy-pent-3-enyl)-thiazol-4-yl]-3-hydroxy-1-((S)-4-isopropyl-2-thioxo-thiazolidin-3-yl)-hexan-1-one

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

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

Downstream raw materials:

(-)-pateamine

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