(2R,3S)-N-(benzyloxycarbonyl)-AHAP-(3-amino-2-hydroxy-4-phenylbutanoic acid) ethyl ester

Base Information

• Chemical Name: (2R,3S)-N-(benzyloxycarbonyl)-AHAP-(3-amino-2-hydroxy-4-phenylbutanoic acid) ethyl ester
• CAS No.: 172696-22-9
• Molecular Formula: C₂₀H₂₃NO₅
• Molecular Weight: 357.406
• Mol file: 172696-22-9.mol

Synonyms:(2R,3S)-N-(benzyloxycarbonyl)-AHAP-(3-amino-2-hydroxy-4-phenylbutanoic acid) ethyl ester

Chemical Property of (2R,3S)-N-(benzyloxycarbonyl)-AHAP-(3-amino-2-hydroxy-4-phenylbutanoic acid) ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S)-N-(benzyloxycarbonyl)-AHAP-(3-amino-2-hydroxy-4-phenylbutanoic acid) ethyl ester

There total 3 articles about (2R,3S)-N-(benzyloxycarbonyl)-AHAP-(3-amino-2-hydroxy-4-phenylbutanoic acid) ethyl 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:

β-<<(phenylmethoxy)carbonyl>amino>-α-oxobenzenebutanoic acid ethyl ester (121253-57-4) → (2S,3S)-N-(benzyloxycarbonyl)-AHAP-(3-amino-2-hydroxy-4-phenylbutanoic acid) ethyl ester (172696-23-0) + (2R,3S)-N-(benzyloxycarbonyl)-AHAP-(3-amino-2-hydroxy-4-phenylbutanoic acid) ethyl ester (172696-22-9)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 0 ℃; for 0.333333h; Yield given. Yields of byproduct given;

DOI:10.1021/ja00153a008

Reference yield:

2-ethoxy-5-phenyl-4-<<(phenylmethoxy)carbonyl>amino>-3-oxo-1-pentene (121253-53-0) → (2R,3S)-N-(benzyloxycarbonyl)-AHAP-(3-amino-2-hydroxy-4-phenylbutanoic acid) ethyl ester (172696-22-9)

Guidance literature:

Multi-step reaction with 2 steps

1: O₃ / CH₂Cl₂

2: NaBH₄ / methanol / 0.33 h / 0 °C

With sodium tetrahydroborate; ozone; In methanol; dichloromethane;

DOI:10.1021/ja00153a008

Reference yield:

[(S)-1-(methoxy-methyl-carbamoyl)-2-phenyl-ethyl]-carbamic acid benzyl ester (114744-85-3) → (2R,3S)-N-(benzyloxycarbonyl)-AHAP-(3-amino-2-hydroxy-4-phenylbutanoic acid) ethyl ester (172696-22-9)

Guidance literature:

Multi-step reaction with 3 steps

1: t-BuLi, MgBr₂ / tetrahydrofuran

2: O₃ / CH₂Cl₂

3: NaBH₄ / methanol / 0.33 h / 0 °C

With sodium tetrahydroborate; tert.-butyl lithium; ozone; magnesium bromide; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/ja00153a008

upstream raw materials:

β-<<(phenylmethoxy)carbonyl>amino>-α-oxobenzenebutanoic acid ethyl ester

2-ethoxy-5-phenyl-4-<<(phenylmethoxy)carbonyl>amino>-3-oxo-1-pentene

[(S)-1-(methoxy-methyl-carbamoyl)-2-phenyl-ethyl]-carbamic acid benzyl ester

Downstream raw materials:

(2R,3S)-N-(benzyloxycarbonyl)-3-amino-2-hydroxy-4-phenylbutanoic acid

(2S,3S)-3-benzyloxycarbonylamino-2-hydroxy-4-phenylbutanoic acid

1-<(2R,3S)-3-benzyloxycarbonylamino-2-hydroxy-4-phenylbutyryl>-N-tert-butyl-L-prolinamide