(S)-5-(2-Bromo-benzyloxy)-3-hydroxy-1-((S)-4-isopropyl-2-thioxo-thiazolidin-3-yl)-pentan-1-one

Base Information

• Chemical Name: (S)-5-(2-Bromo-benzyloxy)-3-hydroxy-1-((S)-4-isopropyl-2-thioxo-thiazolidin-3-yl)-pentan-1-one
• CAS No.: 194342-72-8
• Molecular Formula: C₁₈H₂₄BrNO₃S₂
• Molecular Weight: 446.429
• Mol file: 194342-72-8.mol

Synonyms:(S)-5-(2-Bromo-benzyloxy)-3-hydroxy-1-((S)-4-isopropyl-2-thioxo-thiazolidin-3-yl)-pentan-1-one

Chemical Property of (S)-5-(2-Bromo-benzyloxy)-3-hydroxy-1-((S)-4-isopropyl-2-thioxo-thiazolidin-3-yl)-pentan-1-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-5-(2-Bromo-benzyloxy)-3-hydroxy-1-((S)-4-isopropyl-2-thioxo-thiazolidin-3-yl)-pentan-1-one

There total 4 articles about (S)-5-(2-Bromo-benzyloxy)-3-hydroxy-1-((S)-4-isopropyl-2-thioxo-thiazolidin-3-yl)-pentan-1-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: 83.0%

(S)-3-acetyl-4-isopropyl-1,3-thiazolidine-2-thione (101979-45-7) + 3-(2-Bromo-benzyloxy)-propionaldehyde (194342-71-7) → (S)-5-(2-Bromo-benzyloxy)-3-hydroxy-1-((S)-4-isopropyl-2-thioxo-thiazolidin-3-yl)-pentan-1-one (194342-72-8)

Guidance literature:

With 1-ethyl-piperidine; tin(II) trifluoromethanesulfonate; In dichloromethane; 1.) -50 deg C to -40 deg C, 4 h; 2.) -78 deg C, 4 h;

DOI:10.1016/S0040-4039(97)01140-4

Reference yield:

o-bromobenzyl alcohol (18982-54-2) → (S)-5-(2-Bromo-benzyloxy)-3-hydroxy-1-((S)-4-isopropyl-2-thioxo-thiazolidin-3-yl)-pentan-1-one (194342-72-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 96 percent / NaH / tetrahydrofuran / 4 h / Ambient temperature

2: 1.) 9-BBN; 2.) NaOH, H₂O₂ / 1.) THF, irrad., r.t., 3 h; 2.) reflux, 1 h

3: 76 percent / PCC, Celite / CH₂Cl₂ / 4 h / Ambient temperature

4: 83 percent / 1.) Sn(OTf)2, N-ethylpiperidine / CH₂Cl₂ / 1.) -50 deg C to -40 deg C, 4 h; 2.) -78 deg C, 4 h

With 1-ethyl-piperidine; sodium hydroxide; tin(II) trifluoromethanesulfonate; 9-borabicyclo[3.3.1]nonane dimer; Celite; dihydrogen peroxide; sodium hydride; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4039(97)01140-4

Reference yield:

1-((allyloxy)methyl)-2-bromobenzene (87280-01-1) → (S)-5-(2-Bromo-benzyloxy)-3-hydroxy-1-((S)-4-isopropyl-2-thioxo-thiazolidin-3-yl)-pentan-1-one (194342-72-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) 9-BBN; 2.) NaOH, H₂O₂ / 1.) THF, irrad., r.t., 3 h; 2.) reflux, 1 h

2: 76 percent / PCC, Celite / CH₂Cl₂ / 4 h / Ambient temperature

3: 83 percent / 1.) Sn(OTf)2, N-ethylpiperidine / CH₂Cl₂ / 1.) -50 deg C to -40 deg C, 4 h; 2.) -78 deg C, 4 h

With 1-ethyl-piperidine; sodium hydroxide; tin(II) trifluoromethanesulfonate; 9-borabicyclo[3.3.1]nonane dimer; Celite; dihydrogen peroxide; pyridinium chlorochromate; In dichloromethane;

DOI:10.1016/S0040-4039(97)01140-4

upstream raw materials:

(S)-3-acetyl-4-isopropyl-1,3-thiazolidine-2-thione

3-(2-Bromo-benzyloxy)-propionaldehyde

o-bromobenzyl alcohol

1-((allyloxy)methyl)-2-bromobenzene

Downstream raw materials:

(S)-5-(2-Bromo-benzyloxy)-3-hydroxy-pentanoic acid methoxy-methyl-amide

(S)-5-(2-Bromo-benzyloxy)-3-(tetrahydro-pyran-2-yloxy)-pentanal

(S)-5-(2-Bromo-benzyloxy)-3-(tetrahydro-pyran-2-yloxy)-pentanoic acid methoxy-methyl-amide

(3S,5S)-7-(2-Bromo-benzyloxy)-3-hydroxy-5-(tetrahydro-pyran-2-yloxy)-heptanoic acid methoxy-methyl-amide