(3S,5R)-3-amino-1-((benzyloxy)carbonyl)-5-(tert-butoxycarbonyl)pyrrolidine-3-carboxylic acid

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Chemical Name:(3S,5R)-3-amino-1-((benzyloxy)carbonyl)-5-(tert-butoxycarbonyl)pyrrolidine-3-carboxylic acid
CAS No.:900149-04-4
Molecular Formula:C₁₈H₂₄N₂O₆
Molecular Weight:364.398
Hs Code.:

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

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

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

There total 7 articles about (3S,5R)-3-amino-1-((benzyloxy)carbonyl)-5-(tert-butoxycarbonyl)pyrrolidine-3-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: 73.0%

: 870097-45-3
(5S,8R)-2,4-dioxo-1,3,7-triaza-spiro[4.4]nonane-7,8-dicarboxylic acid 7-benzyl ester 8-tert-butyl ester

: 900149-04-4
(3S,5R)-3-amino-1-((benzyloxy)carbonyl)-5-(tert-butoxycarbonyl)pyrrolidine-3-carboxylic acid

Guidance literature:: (5S,8R)-2,4-dioxo-1,3,7-triaza-spiro[4.4]nonane-7,8-dicarboxylic acid 7-benzyl ester 8-tert-butyl ester; With dmap; di-tert-butyl dicarbonate; In tetrahydrofuran; for 4h; cooling;

With potassium hydroxide; In tetrahydrofuran; water; at 20 ℃;
DOI:10.1021/ol060902q

Reference yield:

: C₂₉H₃₉N₃O₁₀

: 900149-04-4
(3S,5R)-3-amino-1-((benzyloxy)carbonyl)-5-(tert-butoxycarbonyl)pyrrolidine-3-carboxylic acid

Guidance literature:: With potassium hydroxide; In tetrahydrofuran; for 3h; Cooling with ice;
DOI:10.1016/j.tetlet.2016.09.032

Reference yield:

: 51-35-4,30724-02-8
4R-4-hydroxyproline

: 900149-04-4
(3S,5R)-3-amino-1-((benzyloxy)carbonyl)-5-(tert-butoxycarbonyl)pyrrolidine-3-carboxylic acid

Guidance literature:: Multi-step reaction with 7 steps

1.1: acetic anhydride / acetic acid / 24 h / Reflux

1.2: 24 h / Reflux

2.1: sodium hydrogencarbonate / water; 1,4-dioxane

3.1: Jones reagent / acetone / 12 h / Cooling with ice

4.1: sulfuric acid / dichloromethane / 12 h / Cooling with ice

5.1: water; ethanol / 72 h / Sealed tube

6.1: dmap / tetrahydrofuran / 12 h

7.1: potassium hydroxide / tetrahydrofuran / 3 h / Cooling with ice

With dmap; Jones reagent; sulfuric acid; acetic anhydride; sodium hydrogencarbonate; potassium hydroxide; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; water; acetic acid; acetone; 5.1: |Bucherer-Bergs Reaction;
DOI:10.1016/j.tetlet.2016.09.032