(2S,3S)-2-{[(S)-1-((S)-2-Benzyloxycarbonylamino-3-phenyl-propionyl)-pyrrolidine-2-carbonyl]-amino}-3-hydroxy-butyric acid methyl ester

Base Information

Chemical Name:(2S,3S)-2-{[(S)-1-((S)-2-Benzyloxycarbonylamino-3-phenyl-propionyl)-pyrrolidine-2-carbonyl]-amino}-3-hydroxy-butyric acid methyl ester
CAS No.:184295-93-0
Molecular Formula:C₂₇H₃₃N₃O₇
Molecular Weight:511.575
Hs Code.:

Synonyms:(2S,3S)-2-{[(S)-1-((S)-2-Benzyloxycarbonylamino-3-phenyl-propionyl)-pyrrolidine-2-carbonyl]-amino}-3-hydroxy-butyric acid methyl ester

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Chemical Property of (2S,3S)-2-{[(S)-1-((S)-2-Benzyloxycarbonylamino-3-phenyl-propionyl)-pyrrolidine-2-carbonyl]-amino}-3-hydroxy-butyric acid methyl ester

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Technology Process of (2S,3S)-2-{[(S)-1-((S)-2-Benzyloxycarbonylamino-3-phenyl-propionyl)-pyrrolidine-2-carbonyl]-amino}-3-hydroxy-butyric acid methyl ester

There total 7 articles about (2S,3S)-2-{[(S)-1-((S)-2-Benzyloxycarbonylamino-3-phenyl-propionyl)-pyrrolidine-2-carbonyl]-amino}-3-hydroxy-butyric acid methyl 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:

: 1161-13-3
N-Cbz-L-Phe

: 184295-93-0
(2S,3S)-2-{[(S)-1-((S)-2-Benzyloxycarbonylamino-3-phenyl-propionyl)-pyrrolidine-2-carbonyl]-amino}-3-hydroxy-butyric acid methyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: N-methylmorpholine / CH₂Cl₂ / 0.25 h / -15 °C

2: CH₂Cl₂ / 0 - 20 °C

3: aq. LiOH / tetrahydrofuran / 0 - 22 °C

4: N-methylmorpholine / CH₂Cl₂ / 0.25 h / -15 °C

5: CH₂Cl₂ / 0 - 20 °C

6: 891 mg / Et₃N-SO₂NCOOMe / tetrahydrofuran / 2 h / 75 °C

7: 1.) 0.3M aq. HCl, 2.) K₂CO₃ / 1.) THF, 10 min, 2.) THF, 2 h

With 4-methyl-morpholine; hydrogenchloride; lithium hydroxide; Burgess Reagent; potassium carbonate; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ja962859f

Reference yield:

: 41518-17-6
Z-Phe-O-COO-isoBu

: 184295-93-0
(2S,3S)-2-{[(S)-1-((S)-2-Benzyloxycarbonylamino-3-phenyl-propionyl)-pyrrolidine-2-carbonyl]-amino}-3-hydroxy-butyric acid methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: CH₂Cl₂ / 0 - 20 °C

2: aq. LiOH / tetrahydrofuran / 0 - 22 °C

3: N-methylmorpholine / CH₂Cl₂ / 0.25 h / -15 °C

4: CH₂Cl₂ / 0 - 20 °C

5: 891 mg / Et₃N-SO₂NCOOMe / tetrahydrofuran / 2 h / 75 °C

6: 1.) 0.3M aq. HCl, 2.) K₂CO₃ / 1.) THF, 10 min, 2.) THF, 2 h

With 4-methyl-morpholine; hydrogenchloride; lithium hydroxide; Burgess Reagent; potassium carbonate; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ja962859f

Reference yield:

: 28426-51-9
methyl ((benzyloxy)carbonyl)-L-phenylalanyl-L-prolinate

: 184295-93-0
(2S,3S)-2-{[(S)-1-((S)-2-Benzyloxycarbonylamino-3-phenyl-propionyl)-pyrrolidine-2-carbonyl]-amino}-3-hydroxy-butyric acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: aq. LiOH / tetrahydrofuran / 0 - 22 °C

2: N-methylmorpholine / CH₂Cl₂ / 0.25 h / -15 °C

3: CH₂Cl₂ / 0 - 20 °C

4: 891 mg / Et₃N-SO₂NCOOMe / tetrahydrofuran / 2 h / 75 °C

5: 1.) 0.3M aq. HCl, 2.) K₂CO₃ / 1.) THF, 10 min, 2.) THF, 2 h

With 4-methyl-morpholine; hydrogenchloride; lithium hydroxide; Burgess Reagent; potassium carbonate; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ja962859f