(1R,2R,3S,4S)-2-((R)-Benzenesulfinyl)-3-methyl-1-phenyl-pentane-1,4-diol

Base Information

• Chemical Name: (1R,2R,3S,4S)-2-((R)-Benzenesulfinyl)-3-methyl-1-phenyl-pentane-1,4-diol
• CAS No.: 78855-52-4
• Molecular Formula: C₁₈H₂₂O₃S
• Molecular Weight: 318.437
• Mol file: 78855-52-4.mol

Synonyms:(1R,2R,3S,4S)-2-((R)-Benzenesulfinyl)-3-methyl-1-phenyl-pentane-1,4-diol

Chemical Property of (1R,2R,3S,4S)-2-((R)-Benzenesulfinyl)-3-methyl-1-phenyl-pentane-1,4-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2R,3S,4S)-2-((R)-Benzenesulfinyl)-3-methyl-1-phenyl-pentane-1,4-diol

There total 15 articles about (1R,2R,3S,4S)-2-((R)-Benzenesulfinyl)-3-methyl-1-phenyl-pentane-1,4-diol 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:

(+/-)-threo-4-(Phenylthio)-3-methyl-2-butanol (78837-34-0) → (1R,2R,3S,4S)-2-((R)-Benzenesulfinyl)-3-methyl-1-phenyl-pentane-1,4-diol (78855-52-4)

Guidance literature:

Multi-step reaction with 3 steps

1: NaIO₄ / methanol; H₂O; tetrahydrofuran / 22 °C

2: Lithium Diisopropylamide / tetrahydrofuran / 0.02 h / -78 °C

3: 0.01 h

With sodium periodate; lithium diisopropyl amide; In tetrahydrofuran; methanol; water;

DOI:10.1021/jo00333a045

Reference yield:

1-<2(S)-methyl-3(S)-hydroxy>butylphenyl (R)-sulfoxide (78822-84-1) → (1R,2R,3S,4S)-2-((R)-Benzenesulfinyl)-3-methyl-1-phenyl-pentane-1,4-diol (78855-52-4)

Guidance literature:

Multi-step reaction with 2 steps

1: Lithium Diisopropylamide / tetrahydrofuran / 0.02 h / -78 °C

2: 0.01 h

With lithium diisopropyl amide; In tetrahydrofuran;

DOI:10.1021/jo00333a045

Reference yield:

methyl-phenyl-thioether (100-68-5) → (+/-)-(1S*, 2R*, 3R*, 4S*)-3-methyl-1-phenyl-2-((S*)-phenylsulfinyl)-1,4-pentanediol (78822-86-3,78855-52-4,78855-53-5,78855-54-6,78855-55-7,78855-56-8,78855-60-4,78855-61-5,78855-62-6,78855-63-7,78855-64-8,78855-65-9,106454-19-7,106454-20-0,106454-21-1,106454-23-3,106454-24-4,106454-25-5,111002-03-0,111002-05-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) t-BuLi, HMPA / 1.) THF, -78 deg C; 2.) THF, -60 deg C

2: 95 percent / meta-peroxidate / methanol; H₂O; tetrahydrofuran / 24 h / 22 °C

3: 1.) lithium diisopropylamide / 1.) THF, - 78 deg C, 1 min.; 2.) THF, -78 deg C, 1 min.

With N,N,N,N,N,N-hexamethylphosphoric triamide; meta-peroxidate; tert.-butyl lithium; lithium diisopropyl amide; In tetrahydrofuran; methanol; water;

DOI:10.1016/S0040-4020(01)90591-5

upstream raw materials:

C₁₁H₁₅LiO₂S

benzaldehyde

(+/-)-threo-4-(Phenylthio)-3-methyl-2-butanol

1-<2(S)-methyl-3(S)-hydroxy>butylphenyl (R)-sulfoxide

Downstream raw materials:

(+/-)-(2S^*, 3S^*, 4S^*, 5R^*)-tetrahydro-2,3-dimethyl-5-phenyl-4-(phenylthio)furan

(1S,2R,3S,4R)-3-Methyl-1-phenyl-2-phenylsulfanyl-pentane-1,4-diol

(+/-)-(1R^*, 2S^*, 3S^*, 4S^*)-3-methyl-1-phenyl-2-(phenylthio)-1,4-pentanediol

(+/-)-(1R^*, 3R^*, 4S^*)-3-methyl-1-phenyl-1,4-pentadienol