1-[1-bromo-2-hydroxy-(1S)-ethyl]-3-hydroxy-4-phenylsulfonyl-(1R,3S)-butyl alcohol

Base Information

• Chemical Name: 1-[1-bromo-2-hydroxy-(1S)-ethyl]-3-hydroxy-4-phenylsulfonyl-(1R,3S)-butyl alcohol
• CAS No.: 577749-36-1
• Molecular Formula: C₁₂H₁₇BrO₅S
• Molecular Weight: 353.234
• Mol file: 577749-36-1.mol

Synonyms:1-[1-bromo-2-hydroxy-(1S)-ethyl]-3-hydroxy-4-phenylsulfonyl-(1R,3S)-butyl alcohol

Chemical Property of 1-[1-bromo-2-hydroxy-(1S)-ethyl]-3-hydroxy-4-phenylsulfonyl-(1R,3S)-butyl alcohol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-[1-bromo-2-hydroxy-(1S)-ethyl]-3-hydroxy-4-phenylsulfonyl-(1R,3S)-butyl alcohol

There total 11 articles about 1-[1-bromo-2-hydroxy-(1S)-ethyl]-3-hydroxy-4-phenylsulfonyl-(1R,3S)-butyl alcohol 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: 70.0%

(2S,3R,5S)-6-Benzenesulfonyl-2-bromo-1,5-bis-(tert-butyl-diphenyl-silanyloxy)-hexan-3-ol (577749-35-0) → 1-[1-bromo-2-hydroxy-(1S)-ethyl]-3-hydroxy-4-phenylsulfonyl-(1R,3S)-butyl alcohol (577749-36-1)

Guidance literature:

With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; at 20 ℃; for 12h;

DOI:10.1021/jo026892y

Reference yield:

thiophenol (108-98-5) → 1-[1-bromo-2-hydroxy-(1S)-ethyl]-3-hydroxy-4-phenylsulfonyl-(1R,3S)-butyl alcohol (577749-36-1)

Guidance literature:

Multi-step reaction with 8 steps

1: 85 percent / acetonitrile / 2 h / 20 °C

2: 80 percent / DDQ / CH₂Cl₂; H₂O / 5 h / 20 °C

3: 78 percent / LiAlH₄ / tetrahydrofuran / 20 - 60 °C

4: 96 percent / imidazole / CH₂Cl₂ / 12 h / 20 °C

5: 85 percent / NaIO₄ / methanol; tetrahydrofuran; H₂O / 24 h / 20 °C

6: 75 percent / N-bromosuccinimide; H₂O / toluene / 20 °C

7: 90 percent / m-CPBA / CH₂Cl₂ / 20 °C

8: 70 percent / TBAF; acetic acid / tetrahydrofuran / 12 h / 20 °C

With 1H-imidazole; sodium periodate; N-Bromosuccinimide; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; water; acetic acid; 3-chloro-benzenecarboperoxoic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; dichloromethane; water; toluene; acetonitrile;

DOI:10.1021/jo026892y

Reference yield:

1-(4-methoxybenzyloxy)-4-[(2S)-oxiran-2-yl]-2-butyne (272776-88-2) → 1-[1-bromo-2-hydroxy-(1S)-ethyl]-3-hydroxy-4-phenylsulfonyl-(1R,3S)-butyl alcohol (577749-36-1)

Guidance literature:

Multi-step reaction with 8 steps

1: 85 percent / acetonitrile / 2 h / 20 °C

2: 80 percent / DDQ / CH₂Cl₂; H₂O / 5 h / 20 °C

3: 78 percent / LiAlH₄ / tetrahydrofuran / 20 - 60 °C

4: 96 percent / imidazole / CH₂Cl₂ / 12 h / 20 °C

5: 85 percent / NaIO₄ / methanol; tetrahydrofuran; H₂O / 24 h / 20 °C

6: 75 percent / N-bromosuccinimide; H₂O / toluene / 20 °C

7: 90 percent / m-CPBA / CH₂Cl₂ / 20 °C

8: 70 percent / TBAF; acetic acid / tetrahydrofuran / 12 h / 20 °C

With 1H-imidazole; sodium periodate; N-Bromosuccinimide; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; water; acetic acid; 3-chloro-benzenecarboperoxoic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; dichloromethane; water; toluene; acetonitrile;

DOI:10.1021/jo026892y

upstream raw materials:

(2S,3R,5S)-6-Benzenesulfonyl-2-bromo-1,5-bis-(tert-butyl-diphenyl-silanyloxy)-hexan-3-ol

thiophenol

1-(4-methoxybenzyloxy)-4-[(2S)-oxiran-2-yl]-2-butyne

6-phenylsulfanyl-(E,2S)-2-hexene-1,5-diol

Downstream raw materials:

5-bromo-6-t-butyldiphenylsilyloxy-1-phenylsulfonyl-(2S,4R,5S)-hexane-2,4-diol