(2R,3S,4S)-1-tert-butoxycarbonyl-3-benzoyloxy-4-methylpyrrolidine-2-carboxylic acid

Base Information

Chemical Name:(2R,3S,4S)-1-tert-butoxycarbonyl-3-benzoyloxy-4-methylpyrrolidine-2-carboxylic acid
CAS No.:208709-17-5
Molecular Formula:C₁₈H₂₃NO₆
Molecular Weight:349.384
Hs Code.:

Synonyms:(2R,3S,4S)-1-tert-butoxycarbonyl-3-benzoyloxy-4-methylpyrrolidine-2-carboxylic acid

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Chemical Property of (2R,3S,4S)-1-tert-butoxycarbonyl-3-benzoyloxy-4-methylpyrrolidine-2-carboxylic acid

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Technology Process of (2R,3S,4S)-1-tert-butoxycarbonyl-3-benzoyloxy-4-methylpyrrolidine-2-carboxylic acid

There total 16 articles about (2R,3S,4S)-1-tert-butoxycarbonyl-3-benzoyloxy-4-methylpyrrolidine-2-carboxylic acid 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: 88.0%

: 208709-15-3
(2R,3S,4S)-1-tert-butoxycarbonyl-3-benzoyloxy-2-hydroxymethyl-4-methylpyrrolidine

: 208709-17-5
(2R,3S,4S)-1-tert-butoxycarbonyl-3-benzoyloxy-4-methylpyrrolidine-2-carboxylic acid

Guidance literature:: With ruthenium trichloride; sodium periodate; In tetrachloromethane; acetonitrile;
DOI:10.1016/S0957-4166(98)00112-8

Reference yield: 86.0%

: 121964-38-3
3-benzyloxy-2-hydroxymethyl-4-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester

: 208709-17-5
(2R,3S,4S)-1-tert-butoxycarbonyl-3-benzoyloxy-4-methylpyrrolidine-2-carboxylic acid

Guidance literature:: With ruthenium trichloride; sodium periodate; In water; ethyl acetate; at 20 ℃; for 1h;
DOI:10.1016/j.tetlet.2006.10.137

Reference yield:

: 922524-54-7
4-(1,3-dihydroxy-2-methyl-propyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

: 208709-17-5
(2R,3S,4S)-1-tert-butoxycarbonyl-3-benzoyloxy-4-methylpyrrolidine-2-carboxylic acid

Guidance literature:: Multi-step reaction with 6 steps

1: 90 percent / Et₃N / DMAP / CH₂Cl₂ / 6 h / 0 °C

2: 91 percent / NaH / dimethylformamide / 1 h / 0 - 20 °C

3: 89 percent / TBAF / tetrahydrofuran / 3 h / 0 - 20 °C

4: 97 percent / Et₃N / CH₂Cl₂ / 6 h / 0 °C

5: 76 percent / p-TsOH / methanol / 3 h / 20 °C

6: 86 percent / NaIO₄; RuCl₃ / H₂O; ethyl acetate / 1 h / 20 °C

With ruthenium trichloride; sodium periodate; tetrabutyl ammonium fluoride; sodium hydride; toluene-4-sulfonic acid; triethylamine; dmap; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1016/j.tetlet.2006.10.137