(2R,3S,5S)-3-tert-butyldimethylsilyloxy-1-benzyloxycarbonyl-5-β-bromoethylproline tert-butyl ester

Base Information

Chemical Name:(2R,3S,5S)-3-tert-butyldimethylsilyloxy-1-benzyloxycarbonyl-5-β-bromoethylproline tert-butyl ester
CAS No.:221677-06-1
Molecular Formula:C₂₅H₄₀BrNO₅Si
Molecular Weight:542.586
Hs Code.:

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

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

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

There total 11 articles about (2R,3S,5S)-3-tert-butyldimethylsilyloxy-1-benzyloxycarbonyl-5-β-bromoethylproline 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: 96.0%

: 221677-05-0
(2R,3S,5S)-3-tert-butyldimethylsilyloxy-1-benzyloxycarbonyl-5-β-hydroxyethylproline tert-butyl ester

: 221677-06-1
(2R,3S,5S)-3-tert-butyldimethylsilyloxy-1-benzyloxycarbonyl-5-β-bromoethylproline 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

: 221677-06-1
(2R,3S,5S)-3-tert-butyldimethylsilyloxy-1-benzyloxycarbonyl-5-β-bromoethylproline tert-butyl ester

Guidance literature:: Multi-step reaction with 10 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: 78 percent / Et₄NBr, 4-phenylphenol / acetonitrile / electrolysis at 13 mA for 6 h, then - at 1.4 mA

9: 85 percent / aq. K₂CO₃ / ethyl acetate

10: 96 percent / CBr₄, PPh₃ / CH₂Cl₂ / 2 h / Ambient temperature

With 1H-imidazole; hydrogenchloride; ruthenium trichloride; sodium periodate; lithium borohydride; carbon tetrabromide; 4-Phenylphenol; tetraethylammonium bromide; sodium hydride; potassium carbonate; acetic acid; triphenylphosphine; In tetrahydrofuran; methanol; tetrachloromethane; diethyl ether; dichloromethane; water; ethyl acetate; 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

: 221677-06-1
(2R,3S,5S)-3-tert-butyldimethylsilyloxy-1-benzyloxycarbonyl-5-β-bromoethylproline tert-butyl ester

Guidance literature:: Multi-step reaction with 8 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: 78 percent / Et₄NBr, 4-phenylphenol / acetonitrile / electrolysis at 13 mA for 6 h, then - at 1.4 mA

7: 85 percent / aq. K₂CO₃ / ethyl acetate

8: 96 percent / CBr₄, PPh₃ / CH₂Cl₂ / 2 h / Ambient temperature

With 1H-imidazole; ruthenium trichloride; sodium periodate; lithium borohydride; carbon tetrabromide; 4-Phenylphenol; tetraethylammonium bromide; potassium carbonate; acetic acid; triphenylphosphine; In tetrahydrofuran; tetrachloromethane; diethyl ether; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol;
DOI:10.1021/jo982327c