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
Hs Code.:

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

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

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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%

: 577749-35-0
(2S,3R,5S)-6-Benzenesulfonyl-2-bromo-1,5-bis-(tert-butyl-diphenyl-silanyloxy)-hexan-3-ol

: 577749-36-1
1-[1-bromo-2-hydroxy-(1S)-ethyl]-3-hydroxy-4-phenylsulfonyl-(1R,3S)-butyl alcohol

Guidance literature:: With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; at 20 ℃; for 12h;
DOI:10.1021/jo026892y

Reference yield:

: 108-98-5
thiophenol

: 577749-36-1
1-[1-bromo-2-hydroxy-(1S)-ethyl]-3-hydroxy-4-phenylsulfonyl-(1R,3S)-butyl alcohol

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:

: 272776-88-2
1-(4-methoxybenzyloxy)-4-[(2S)-oxiran-2-yl]-2-butyne

: 577749-36-1
1-[1-bromo-2-hydroxy-(1S)-ethyl]-3-hydroxy-4-phenylsulfonyl-(1R,3S)-butyl alcohol

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