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

Base Information

Chemical Name:(2R,3S,5S)-3-tert-butyldimethylsilyloxy-1-benzyloxycarbonyl-5-β-hydroxyethylproline tert-butyl ester
CAS No.:221677-05-0
Molecular Formula:C₂₅H₄₁NO₆Si
Molecular Weight:479.689
Hs Code.:

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

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

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

There total 10 articles about (2R,3S,5S)-3-tert-butyldimethylsilyloxy-1-benzyloxycarbonyl-5-β-hydroxyethylproline 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: 85.0%

: 501-53-1,94274-21-2
benzyl chloroformate

: 221677-04-9
(2R,3S,5S)-3-tert-butyldimethylsilyloxy-5-β-hydroxyethylproline tert-butyl ester

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

Guidance literature:: With potassium carbonate; In ethyl acetate;
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

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

Guidance literature:: Multi-step reaction with 9 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

With 1H-imidazole; hydrogenchloride; ruthenium trichloride; sodium periodate; lithium borohydride; 4-Phenylphenol; tetraethylammonium bromide; sodium hydride; potassium carbonate; acetic acid; 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

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

Guidance literature:: Multi-step reaction with 7 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

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