[(1S,2R,3R)-1-Benzyl-2-hydroxy-3-[(S)-1-(2-hydroxy-4-methoxy-benzylcarbamoyl)-2-methyl-propylcarbamoyl]-3-(3-methoxy-benzylamino)-propyl]-carbamic acid tert-butyl ester

Base Information

• Chemical Name: [(1S,2R,3R)-1-Benzyl-2-hydroxy-3-[(S)-1-(2-hydroxy-4-methoxy-benzylcarbamoyl)-2-methyl-propylcarbamoyl]-3-(3-methoxy-benzylamino)-propyl]-carbamic acid tert-butyl ester
• CAS No.: 376644-31-4
• Molecular Formula: C₃₇H₅₀N₄O₈
• Molecular Weight: 678.826

Synonyms:

Chemical Property of [(1S,2R,3R)-1-Benzyl-2-hydroxy-3-[(S)-1-(2-hydroxy-4-methoxy-benzylcarbamoyl)-2-methyl-propylcarbamoyl]-3-(3-methoxy-benzylamino)-propyl]-carbamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Useful:

Technology Process of [(1S,2R,3R)-1-Benzyl-2-hydroxy-3-[(S)-1-(2-hydroxy-4-methoxy-benzylcarbamoyl)-2-methyl-propylcarbamoyl]-3-(3-methoxy-benzylamino)-propyl]-carbamic acid tert-butyl ester

There total 6 articles about [(1S,2R,3R)-1-Benzyl-2-hydroxy-3-[(S)-1-(2-hydroxy-4-methoxy-benzylcarbamoyl)-2-methyl-propylcarbamoyl]-3-(3-methoxy-benzylamino)-propyl]-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:

(S)-2-amino-N-(2-hydroxy-4-methoxybenzyl)-3-methylbutyramide hydrochloride + (2R,3R,4S)-4-tert-butoxycarbonylamino-3-hydroxy-2-(3-methoxy-benzylamino)-5-phenyl-pentanoic acid (376644-30-3) → [(1S,2R,3R)-1-Benzyl-2-hydroxy-3-[(S)-1-(2-hydroxy-4-methoxy-benzylcarbamoyl)-2-methyl-propylcarbamoyl]-3-(3-methoxy-benzylamino)-propyl]-carbamic acid tert-butyl ester (376644-31-4)

Guidance literature:

With O-(1,2-dihydro-2-oxo-1-pyridyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1016/S0960-894X(02)00178-6

Reference yield:

ethyl (2E,4S)-4-[(tert-butoxycarbonyl)amino]-5-phenylpent-2-enoate (124818-94-6,116246-06-1) → [(1S,2R,3R)-1-Benzyl-2-hydroxy-3-[(S)-1-(2-hydroxy-4-methoxy-benzylcarbamoyl)-2-methyl-propylcarbamoyl]-3-(3-methoxy-benzylamino)-propyl]-carbamic acid tert-butyl ester (376644-31-4)

Guidance literature:

Multi-step reaction with 4 steps

1: MCPBA / CH₂Cl₂ / 20 °C

2: ethanol / 70 °C

3: 1 N LiOH / tetrahydrofuran / 20 °C

4: TPTU; DIEA / dimethylformamide / 20 °C

With lithium hydroxide; O-(1,2-dihydro-2-oxo-1-pyridyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0960-894X(02)00178-6

Reference yield:

Boc-L-phenylalaninal (72155-45-4) → [(1S,2R,3R)-1-Benzyl-2-hydroxy-3-[(S)-1-(2-hydroxy-4-methoxy-benzylcarbamoyl)-2-methyl-propylcarbamoyl]-3-(3-methoxy-benzylamino)-propyl]-carbamic acid tert-butyl ester (376644-31-4)

Guidance literature:

Multi-step reaction with 5 steps

1: toluene / 80 °C

2: MCPBA / CH₂Cl₂ / 20 °C

3: ethanol / 70 °C

4: 1 N LiOH / tetrahydrofuran / 20 °C

5: TPTU; DIEA / dimethylformamide / 20 °C

With lithium hydroxide; O-(1,2-dihydro-2-oxo-1-pyridyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0960-894X(02)00178-6

upstream raw materials:

(2R,3R,4S)-4-tert-butoxycarbonylamino-3-hydroxy-2-(3-methoxy-benzylamino)-5-phenyl-pentanoic acid

ethyl (2E,4S)-4-[(tert-butoxycarbonyl)amino]-5-phenylpent-2-enoate

Boc-L-phenylalaninal

(S)-N-tert-butoxycarbonyl-2-amino-3-phenylpropanol

Downstream raw materials:

(2R,3R,4S)-4-Amino-3-hydroxy-2-(3-methoxy-benzylamino)-5-phenyl-pentanoic acid [(S)-1-(2-hydroxy-4-methoxy-benzylcarbamoyl)-2-methyl-propyl]-amide

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