Z-(2R,3S)-AHPA

Base Information

• Chemical Name: Z-(2R,3S)-AHPA
• CAS No.: 59969-65-2
• Molecular Formula: C18H19NO5
• Molecular Weight: 329.353
• Mol file: 59969-65-2.mol

Synonyms:Z-(2S,3R)-AHPA;Z-(2R,3S)-AHPA;2S,3R)-3-(((benzyloxy)carbonyl)-Amino)-2-hydroxy-4-phenylbutyric acid;(2R,3S)-3-(((benzyloxy)carbonyl)aMino)-2-hydroxy-4-phenylbutanoic acid;Benzenebutanoic acid, α-hydroxy-β-[[(phenylmethoxy)carbonyl]amino]-, (αS,βR)-;(alphaS,betaR)-alpha-Hydroxy-beta-[[(phenylmethoxy)carbonyl]amino]benzenebutanoic acid

Chemical Property of Z-(2R,3S)-AHPA

Chemical Property:

• Melting Point: 152-153 oC**
• Boiling Point: 581.9±50.0 °C(Predicted)
• PKA: 3.56±0.17(Predicted)
• PSA: 99.35000
• Density: 1.295±0.06 g/cm3 (20 oC 760 Torr), Calc.*
• LogP: 2.17400
• Storage Temp.: 2-8°C

Purity/Quality:

98%,99%, ^*data from raw suppliers

(2S,3R)-3-(((Benzyloxy)carbonyl)amino)-2-hydroxy-4-phenylbutanoicacid 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Z-(2R,3S)-AHPA

There total 28 articles about Z-(2R,3S)-AHPA 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: 64.0%

(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid (59554-14-2) + benzyl chloroformate (501-53-1,94274-21-2) → (2S,3R)-3-benzyloxycarbonylamino-2-hydroxy-4-phenyl-butanoic acid (59969-65-2,76498-22-1)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; at 20 ℃; for 6h; Cooling with ice;

Reference yield:

benzyl S-4,6-dimethylpyrimidin-2-ylthiocarbonate + (2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid (59554-14-2) → (2S,3R)-3-benzyloxycarbonylamino-2-hydroxy-4-phenyl-butanoic acid (59969-65-2,76498-22-1)

Guidance literature:

With triethylamine; In 1,4-dioxane; water; ethyl acetate;

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:

Bestatin hydrochloride

bestatin

Refernces

• 1、 Seki, Masahiko,Nakao, Kazuya. "Novel synthesis of (-)-bestatin from L-aspartic acid". . p. 1304 - 1307. Retrieved 2007/10/03.
• 2、 Kawabata,Kiryu,Sugiura,Fuji. "An enantiodivergent synthesis of three β-amino alcohols: Preparation of key intermediates for bestatin and the related peptides". . p. 5127 - 5130. Retrieved 2007/10/02.