{(R)-(2-Benzyloxy-4-methoxy-phenyl)-[(1S,2R)-1-{[(S)-(3,5-dimethoxy-phenyl)-methylcarbamoyl-methyl]-carbamoyl}-2-(4-fluoro-3-nitro-phenyl)-2-hydroxy-ethylcarbamoyl]-methyl}-carbamic acid tert-butyl ester

Base Information

• Chemical Name: {(R)-(2-Benzyloxy-4-methoxy-phenyl)-[(1S,2R)-1-{[(S)-(3,5-dimethoxy-phenyl)-methylcarbamoyl-methyl]-carbamoyl}-2-(4-fluoro-3-nitro-phenyl)-2-hydroxy-ethylcarbamoyl]-methyl}-carbamic acid tert-butyl ester
• CAS No.: 218901-87-2
• Molecular Formula: C₄₁H₄₆FN₅O₁₂
• Molecular Weight: 819.841

Synonyms:{(R)-(2-Benzyloxy-4-methoxy-phenyl)-[(1S,2R)-1-{[(S)-(3,5-dimethoxy-phenyl)-methylcarbamoyl-methyl]-carbamoyl}-2-(4-fluoro-3-nitro-phenyl)-2-hydroxy-ethylcarbamoyl]-methyl}-carbamic acid tert-butyl ester

Chemical Property of {(R)-(2-Benzyloxy-4-methoxy-phenyl)-[(1S,2R)-1-{[(S)-(3,5-dimethoxy-phenyl)-methylcarbamoyl-methyl]-carbamoyl}-2-(4-fluoro-3-nitro-phenyl)-2-hydroxy-ethylcarbamoyl]-methyl}-carbamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

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Technology Process of {(R)-(2-Benzyloxy-4-methoxy-phenyl)-[(1S,2R)-1-{[(S)-(3,5-dimethoxy-phenyl)-methylcarbamoyl-methyl]-carbamoyl}-2-(4-fluoro-3-nitro-phenyl)-2-hydroxy-ethylcarbamoyl]-methyl}-carbamic acid tert-butyl ester

There total 10 articles about {(R)-(2-Benzyloxy-4-methoxy-phenyl)-[(1S,2R)-1-{[(S)-(3,5-dimethoxy-phenyl)-methylcarbamoyl-methyl]-carbamoyl}-2-(4-fluoro-3-nitro-phenyl)-2-hydroxy-ethylcarbamoyl]-methyl}-carbamic acid 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:

4-fluoro-3-nitrobenzaldehyde (42564-51-2) → {(R)-(2-Benzyloxy-4-methoxy-phenyl)-[(1S,2R)-1-{[(S)-(3,5-dimethoxy-phenyl)-methylcarbamoyl-methyl]-carbamoyl}-2-(4-fluoro-3-nitro-phenyl)-2-hydroxy-ethylcarbamoyl]-methyl}-carbamic acid tert-butyl ester (218901-87-2)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) Sn(OTf)2, N-ethylpiperidine / 1.) THF, -78 deg C

2: DMAP / CH₂Cl₂

3: HCO₂H, H₂O₂ / H₂O

4: LiOOH / -10 °C

5: EDCI*HCl, HOBt / tetrahydrofuran / 0 °C

6: LiOH / methanol; H₂O

7: TFA, Me₂S / CH₂Cl₂ / 0 °C

8: EDCI*HCl, HOBt / tetrahydrofuran / 0 °C

With 1-ethyl-piperidine; dmap; lithium hydroxide; tin(II) trifluoromethanesulfonate; formic acid; lithium hydroperoxide; dimethylsulfide; dihydrogen peroxide; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1002/(SICI)1521-3773(19981016)37:19<2700::AID-ANIE2700>3.0.CO;2-P

Reference yield:

(2-benzyloxy-4-methoxy-phenyl)-tert-butoxycarbonylamino-acetic acid + (2S,3R)-2-Amino-N-[(S)-(3,5-dimethoxy-phenyl)-methylcarbamoyl-methyl]-3-(4-fluoro-3-nitro-phenyl)-3-hydroxy-propionamide → {(R)-(2-Benzyloxy-4-methoxy-phenyl)-[(1S,2R)-1-{[(S)-(3,5-dimethoxy-phenyl)-methylcarbamoyl-methyl]-carbamoyl}-2-(4-fluoro-3-nitro-phenyl)-2-hydroxy-ethylcarbamoyl]-methyl}-carbamic acid tert-butyl ester (218901-87-2)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; at 0 ℃; Yield given;

DOI:10.1002/(SICI)1521-3773(19981016)37:19<2700::AID-ANIE2700>3.0.CO;2-P

Reference yield:

2-amino-2-(3,5-dimethoxy-phenyl)-N-methyl-acetamide (1026848-12-3) → {(R)-(2-Benzyloxy-4-methoxy-phenyl)-[(1S,2R)-1-{[(S)-(3,5-dimethoxy-phenyl)-methylcarbamoyl-methyl]-carbamoyl}-2-(4-fluoro-3-nitro-phenyl)-2-hydroxy-ethylcarbamoyl]-methyl}-carbamic acid tert-butyl ester (218901-87-2)

Guidance literature:

Multi-step reaction with 4 steps

1: EDCI*HCl, HOBt / tetrahydrofuran / 0 °C

2: LiOH / methanol; H₂O

3: TFA, Me₂S / CH₂Cl₂ / 0 °C

4: EDCI*HCl, HOBt / tetrahydrofuran / 0 °C

With lithium hydroxide; dimethylsulfide; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1002/(SICI)1521-3773(19981016)37:19<2700::AID-ANIE2700>3.0.CO;2-P

upstream raw materials:

4-fluoro-3-nitrobenzaldehyde

2-amino-2-(3,5-dimethoxy-phenyl)-N-methyl-acetamide

(4S,5R)-5-(4-Fluoro-3-nitro-phenyl)-2-oxo-oxazolidine-3,4-dicarboxylic acid 3-tert-butyl ester

(S)-4-Benzyl-3-[(4S,5R)-5-(4-fluoro-3-nitro-phenyl)-2-thioxo-oxazolidine-4-carbonyl]-oxazolidin-2-one

Downstream raw materials:

(2S,3R)-2-[(R)-2-(2-Benzyloxy-4-methoxy-phenyl)-2-(2,2,2-trifluoro-acetylamino)-acetylamino]-N-[(S)-(3,5-dimethoxy-phenyl)-methylcarbamoyl-methyl]-3-(4-fluoro-3-nitro-phenyl)-3-hydroxy-propionamide

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