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

Base Information

Chemical Name:(2R,3S,5S)-3-tert-butyldimethylsilyloxy-5-methoxycarbonylmethyl-1-phenylsulfonylproline tert-butyl ester
CAS No.:221676-99-9
Molecular Formula:C₂₄H₃₉NO₇SSi
Molecular Weight:513.728
Hs Code.:

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

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

Chemical Property:

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

There total 7 articles about (2R,3S,5S)-3-tert-butyldimethylsilyloxy-5-methoxycarbonylmethyl-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:

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

: 221676-99-9
(2R,3S,5S)-3-tert-butyldimethylsilyloxy-5-methoxycarbonylmethyl-1-phenylsulfonylproline tert-butyl ester

Guidance literature:: Multi-step reaction with 6 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

With 1H-imidazole; hydrogenchloride; ruthenium trichloride; sodium periodate; sodium hydride; acetic acid; In tetrahydrofuran; methanol; tetrachloromethane; 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

: 221676-99-9
(2R,3S,5S)-3-tert-butyldimethylsilyloxy-5-methoxycarbonylmethyl-1-phenylsulfonylproline tert-butyl ester

Guidance literature:: Multi-step reaction with 4 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

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

Reference yield:

: 221676-92-2
(2S,4S,5S)-4-hydroxy-5-hydroxymethyl-2-(methoxycarbonyl)methyl-1-(phenylsulfonyl)pyrrolidine isopropylidine ketal

: 221676-99-9
(2R,3S,5S)-3-tert-butyldimethylsilyloxy-5-methoxycarbonylmethyl-1-phenylsulfonylproline tert-butyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 96 percent / aq. HCl / methanol / 24 h / Ambient temperature

2: 96 percent / imidazole / dimethylformamide / 12 h / Ambient temperature

3: 87 percent / aq. AcOH / tetrahydrofuran / 22 h / Ambient temperature

4: 1.04 g / RuCl₃*3H₂O, NaIO₄ / acetonitrile; CCl₄; H₂O / 3 h

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

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