(aR,bS)-rel-alpha-Hydroxy-beta-[[(phenylmethoxy)carbonyl]amino]benzenebutanoic acid

Base Information

• Chemical Name: (aR,bS)-rel-alpha-Hydroxy-beta-[[(phenylmethoxy)carbonyl]amino]benzenebutanoic acid
• CAS No.: 76498-22-1
• Molecular Formula: C₁₈H₁₉NO₅
• Molecular Weight: 329.353
• Mol file: 76498-22-1.mol

Synonyms:Benzenebutanoic acid, alpha-hydroxy-beta-[[(phenylmethoxy)carbonyl]amino]-, (alphaS,betaR)-;

Chemical Property of (aR,bS)-rel-alpha-Hydroxy-beta-[[(phenylmethoxy)carbonyl]amino]benzenebutanoic acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.602
• Boiling Point: 581.871 °C at 760 mmHg
• Flash Point: 305.705 °C
• PSA: 84.86000
• Density: 1.296 g/cm³
• LogP: 2.83900

Purity/Quality:

99% ^*data from raw suppliers

(AR,bS)-rel-a-hydroxy-b-[[(phenylmethoxy)carbonyl]amino]-benzenebutanoicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (aR,bS)-rel-alpha-Hydroxy-beta-[[(phenylmethoxy)carbonyl]amino]benzenebutanoic acid

There total 68 articles about (aR,bS)-rel-alpha-Hydroxy-beta-[[(phenylmethoxy)carbonyl]amino]benzenebutanoic 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: 100.0%

methyl (2S,3R)-3--2-hydroxy-4-phenylbutanoate (124782-04-3) → (2S,3R)-3-benzyloxycarbonylamino-2-hydroxy-4-phenyl-butanoic acid (59969-65-2,76498-22-1)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; water; for 1h; Ambient temperature;

DOI:10.1021/jo00294a047

Reference yield: 100.0%

(2R,3R)-3-(N-(benzyloxycarbonyl)amino)-2-hydroxy-4-phenylbutanoic acid methyl ester (124782-06-5) → (2R,3R)-3-(N-(benzyloxycarbonyl)amino)-2-hydroxy-4-phenylbutanoic acid (62023-58-9,76498-22-1)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; water; for 1h; Ambient temperature;

DOI:10.1021/jo00294a047

Reference yield: 100.0%

(2S,3S)-3-[[(benzyloxy)carbonyl]amino]-2-hydroxy-4-phenylbutanoic acid methyl ester (126015-23-4) → (2S,3S)-3-benzyloxycarbonylamino-2-hydroxy-4-phenylbutanoic acid (62023-59-0,76498-22-1)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; for 1h; Ambient temperature;

DOI:10.1055/s-1989-27367

upstream raw materials:

potassium cyanide

benzyl chloroformate

[(R)-1-Benzyl-2-(3,5-dimethyl-pyrazol-1-yl)-2-oxo-ethyl]-carbamic acid benzyl ester

methyl (2S,3R)-3--2-hydroxy-4-phenylbutanoate

Downstream raw materials:

benzyl N-[(2S,3R)-3-(N-benzyloxycarbonyl)amino-2-hydroxy-4-phenylbutanoyl]-L-leucinate

Z-(2S,3R)-AHPA-(R)-Leu-OBzl

Z-(2S,3S)-AHPA-(S)-Leu-OBzl

Z-(2S,3S)-AHPA-(R)-Leu-OBzl

Refernces

Syntheses of HIV-protease inhibitors having a peptide moiety which binds to GP120

10.1248/cpb.46.697

The research focuses on the synthesis of HIV-protease inhibitors that incorporate a peptide moiety capable of binding to gp120, a protein on the surface of the HIV virus. The study was motivated by the need to develop therapeutic agents to inhibit the replication of HIV, the virus responsible for AIDS. Z-AHPA and phenoxyacetyl chloride are essential components in the synthesis of HIV-protease inhibitors with a peptide moiety designed to bind to gp120. Z-AHPA is prepared from L-Phe according to a reported procedure. Phenoxyacetyl chloride is synthesized by reacting phenoxyacetic acid with thionyl chloride (SOCl2) or another suitable chlorinating agent. Z-AHPA provides the core peptide structure, while phenoxyacetyl chloride enables the introduction of functional groups that enhance the binding properties of the final compounds. The successful incorporation of these components leads to the development of inhibitors with significant anti-HIV activity and protease-inhibitory properties.

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