(2R,3S,5S)-3-tert-butyldimethylsilyloxy-5-β-bromoethyl-1-phenylsulfonylproline tert-butyl ester

Base Information

Chemical Name:(2R,3S,5S)-3-tert-butyldimethylsilyloxy-5-β-bromoethyl-1-phenylsulfonylproline tert-butyl ester
CAS No.:221677-01-6
Molecular Formula:C₂₃H₃₈BrNO₅SSi
Molecular Weight:548.614
Hs Code.:

Synonyms:(2R,3S,5S)-3-tert-butyldimethylsilyloxy-5-β-bromoethyl-1-phenylsulfonylproline tert-butyl ester

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Chemical Property of (2R,3S,5S)-3-tert-butyldimethylsilyloxy-5-β-bromoethyl-1-phenylsulfonylproline tert-butyl ester

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Technology Process of (2R,3S,5S)-3-tert-butyldimethylsilyloxy-5-β-bromoethyl-1-phenylsulfonylproline tert-butyl ester

There total 9 articles about (2R,3S,5S)-3-tert-butyldimethylsilyloxy-5-β-bromoethyl-1-phenylsulfonylproline tert-butyl ester 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: 95.0%

: 221677-00-5
(2R,3S,5S)-3-tert-butyldimethylsilyloxy-5-β-hydroxyethyl-1-phenylsulfonylproline tert-butyl ester

: 221677-01-6
(2R,3S,5S)-3-tert-butyldimethylsilyloxy-5-β-bromoethyl-1-phenylsulfonylproline tert-butyl ester

Guidance literature:: With carbon tetrabromide; triphenylphosphine; In dichloromethane; for 2h; Ambient temperature;
DOI:10.1021/jo982327c

Reference yield:

: 119593-29-2
(4aS,7aS)-5-Benzenesulfonyl-2,2-dimethyl-hexahydro-[1,3]dioxino[5,4-b]pyrrol-6-ol

: 221677-01-6
(2R,3S,5S)-3-tert-butyldimethylsilyloxy-5-β-bromoethyl-1-phenylsulfonylproline tert-butyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: NaH / tetrahydrofuran / 96 h / -15 - -10 °C

2: 96 percent / aq. HCl / methanol / 24 h / Ambient temperature

3: 96 percent / imidazole / dimethylformamide / 12 h / Ambient temperature

4: 87 percent / aq. AcOH / tetrahydrofuran / 22 h / Ambient temperature

5: 1.04 g / RuCl₃*3H₂O, NaIO₄ / acetonitrile; CCl₄; H₂O / 3 h

6: CH₂Cl₂; 2-methyl-propan-2-ol / 1.75 h / Ambient temperature

7: 86 percent / LiBH₄ / diethyl ether; tetrahydrofuran / 8 h

8: 95 percent / CBr₄, Ph₃P / CH₂Cl₂ / 2 h / Ambient temperature

With 1H-imidazole; hydrogenchloride; ruthenium trichloride; sodium periodate; lithium borohydride; carbon tetrabromide; sodium hydride; acetic acid; triphenylphosphine; In tetrahydrofuran; methanol; tetrachloromethane; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol;
DOI:10.1021/jo982327c

Reference yield:

: 221676-96-6
methyl (2S,4S,5S)-4-hydroxy-5-hydroxymethyl-1-phenylsulfonylpyrrolidine-2-acetate

: 221677-01-6
(2R,3S,5S)-3-tert-butyldimethylsilyloxy-5-β-bromoethyl-1-phenylsulfonylproline tert-butyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 96 percent / imidazole / dimethylformamide / 12 h / Ambient temperature

2: 87 percent / aq. AcOH / tetrahydrofuran / 22 h / Ambient temperature

3: 1.04 g / RuCl₃*3H₂O, NaIO₄ / acetonitrile; CCl₄; H₂O / 3 h

4: CH₂Cl₂; 2-methyl-propan-2-ol / 1.75 h / Ambient temperature

5: 86 percent / LiBH₄ / diethyl ether; tetrahydrofuran / 8 h

6: 95 percent / CBr₄, Ph₃P / CH₂Cl₂ / 2 h / Ambient temperature

With 1H-imidazole; ruthenium trichloride; sodium periodate; lithium borohydride; carbon tetrabromide; acetic acid; triphenylphosphine; In tetrahydrofuran; tetrachloromethane; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol;
DOI:10.1021/jo982327c