(2S,3R)-3-(3-(benzyloxy)-5-carboxyphenyl)-1-(tert-butoxycarbonyl)-pyrrolidine-2-carboxylic acid

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Chemical Name:(2S,3R)-3-(3-(benzyloxy)-5-carboxyphenyl)-1-(tert-butoxycarbonyl)-pyrrolidine-2-carboxylic acid
CAS No.:1622154-08-8
Molecular Formula:C₂₄H₂₇NO₇
Molecular Weight:441.481
Hs Code.:

Synonyms:(2S,3R)-3-(3-(benzyloxy)-5-carboxyphenyl)-1-(tert-butoxycarbonyl)-pyrrolidine-2-carboxylic acid

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Chemical Property of (2S,3R)-3-(3-(benzyloxy)-5-carboxyphenyl)-1-(tert-butoxycarbonyl)-pyrrolidine-2-carboxylic acid

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Technology Process of (2S,3R)-3-(3-(benzyloxy)-5-carboxyphenyl)-1-(tert-butoxycarbonyl)-pyrrolidine-2-carboxylic acid

There total 18 articles about (2S,3R)-3-(3-(benzyloxy)-5-carboxyphenyl)-1-(tert-butoxycarbonyl)-pyrrolidine-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: 83.0%

: 1622235-80-6
(2S,3R)-tert-butyl 3-(3-(benzyloxy)-5-(hydroxymethyl)phenyl)-2-(hydroxymethyl)pyrrolidine-1-carboxylate

: 1622154-08-8
(2S,3R)-3-(3-(benzyloxy)-5-carboxyphenyl)-1-(tert-butoxycarbonyl)-pyrrolidine-2-carboxylic acid

Guidance literature:: With sodium periodate; ruthenium(III) trichloride hydrate; In water; ethyl acetate; acetonitrile; at 0 ℃; for 2.08h;

Reference yield: 83.0%

: 1622235-80-6
(2S,3R)-tert-butyl 3-(3-(benzyloxy)-5-(hydroxymethyl)phenyl)-2-(hydroxymethyl)pyrrolidine-1-carboxylate

: 1622154-08-8
(2S,3R)-3-(3-(benzyloxy)-5-carboxyphenyl)-1-(tert-butoxycarbonyl)-pyrrolidine-2-carboxylic acid

: N-BOC-L-trans-2,3-dicarboxypyrrolidine

Guidance literature:: With sodium periodate; ruthenium(III) trichloride hydrate; In water; ethyl acetate; acetonitrile; at 0 ℃; for 2h;
DOI:10.1021/acs.jmedchem.5b00750

Reference yield:

: 17342-08-4
(S)-Pyroglutaminol

: 1622154-08-8
(2S,3R)-3-(3-(benzyloxy)-5-carboxyphenyl)-1-(tert-butoxycarbonyl)-pyrrolidine-2-carboxylic acid

Guidance literature:: Multi-step reaction with 7 steps

1.1: 1H-imidazole / dichloromethane / 24 h / 20 °C

2.1: dmap / acetonitrile / 0 - 20 °C

3.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C

3.2: 0.75 h / -78 °C

3.3: 1.41 h / 0 - 20 °C

4.1: tert.-butyl lithium / diethyl ether / 0.75 h / -78 °C / Inert atmosphere

4.2: 0.42 h / -78 - -42 °C / Inert atmosphere

5.1: borane-THF / tetrahydrofuran / 20.08 h / Inert atmosphere; Reflux

5.2: 0.5 h / 0 °C / Inert atmosphere

5.3: 1.33 h / 20 °C / Inert atmosphere

6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 20 °C

7.1: sodium periodate; ruthenium(III) trichloride hydrate / water; ethyl acetate; acetonitrile / 2.08 h / 0 °C

With 1H-imidazole; dmap; sodium periodate; borane-THF; ruthenium(III) trichloride hydrate; tetrabutyl ammonium fluoride; tert.-butyl lithium; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; dichloromethane; water; ethyl acetate; acetonitrile;