N-BOC-(2R,3R)-2-HYDROXY-3-AMINO-4-PHENYLBUTANOIC ACID

Base Information

• Chemical Name: N-BOC-(2R,3R)-2-HYDROXY-3-AMINO-4-PHENYLBUTANOIC ACID
• CAS No.: 116661-86-0
• Molecular Formula: C₁₅H₂₁NO₅
• Molecular Weight: 295.335
• Mol file: 116661-86-0.mol

Synonyms:Benzenebutanoicacid, b-[[(1,1-dimethylethoxy)carbonyl]amino]-a-hydroxy-, [S-(R*,R*)]-;(2S,3S)-(-)-3-(tert-Butoxycarbonylamino)-2-hydroxy-4-phenylbutanoic acid;(2S,3S)-3-[(tert-Butoxycarbonyl)amino]-2-hydroxy-4-phenylbutyric acid;(2S,3S)-3-tert-Butoxycarbonylamino-2-hydroxy-4-phenylbutanoic acid

Chemical Property of N-BOC-(2R,3R)-2-HYDROXY-3-AMINO-4-PHENYLBUTANOIC ACID

Chemical Property:

• Vapor Pressure: 8.81E-11mmHg at 25°C
• Melting Point: 147-148 °C
• Refractive Index: 1.542
• Boiling Point: 499.1°Cat760mmHg
• PKA: 3.57±0.17(Predicted)
• Flash Point: 255.7°C
• PSA: 95.86000
• Density: 1.215g/cm³
• LogP: 1.95880

Purity/Quality:

99.5% ^*data from raw suppliers

Boc-(2S-3S)-3-amino-2-hydroxy-4-phenylbutyric acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of N-BOC-(2R,3R)-2-HYDROXY-3-AMINO-4-PHENYLBUTANOIC ACID

There total 24 articles about N-BOC-(2R,3R)-2-HYDROXY-3-AMINO-4-PHENYLBUTANOIC 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: 39.0%

aqueous potassium hydroxide + aqueous sodium hypochlorite + dipercarbonate de O,O-t-butyle (3236-56-4) + (2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane (98760-08-8) + sodium hydrogensulfite → (2S,3S)-3-tert-butoxycarbonylamino-2-hydroxy-4-phenylbutanoic acid (62023-65-8,76498-21-0,77171-41-6,82848-28-0,105181-72-4,116661-86-0)

Guidance literature:

With potassium hydroxide; cyfluthrin; In hexane; water; ethyl acetate; acetonitrile;

Reference yield: 32.5%

di-tert-butyl dicarbonate (24424-99-5) + 2(RS)-hydroxy-3(S)-amino-4-phenylbutanoic acid (209173-80-8) → (2S,3S)-3-tert-butoxycarbonylamino-2-hydroxy-4-phenylbutanoic acid (62023-65-8,76498-21-0,77171-41-6,82848-28-0,105181-72-4,116661-86-0) + (2R,3S)-3-tert-butoxycarbonylamino-2-hydroxy-4-phenylbutyric acid (105181-72-4)

Guidance literature:

With TEA; In tetrahydrofuran; water;

DOI:10.1016/S0223-5234(00)00187-2

Reference yield:

(3S)-1,1-dibromo-3-tert-butoxycarbonylamino-4-phenyl-2-butanone (290836-34-9) → (2S,3S)-3-tert-butoxycarbonylamino-2-hydroxy-4-phenylbutanoic acid (62023-65-8,76498-21-0,77171-41-6,82848-28-0,105181-72-4,116661-86-0)

Guidance literature:

With sodium hydroxide; In water; toluene; at 0 ℃; for 21h;

upstream raw materials:

N-(tert-butyloxycarbonyl)-(2S,3S)-3-amino-2-hydroxy-4-phenylbutanoic acid methyl ester

di-tert-butyl dicarbonate

2(RS)-hydroxy-3(S)-amino-4-phenylbutanoic acid

(3S)-3-tert-butoxycarbonylamino-1,1-dichloro-4-phenyl-2-butanone

Downstream raw materials:

N-Boc-(2S,3S)-AHPA-L-Leu-tert-butyl ester

((2S,3S)-3-tert-Butoxycarbonylamino-2-hydroxy-4-phenyl-butyrylamino)-acetic acid tert-butyl ester

[1-benzyl-3-(2-tert-butylcarbamoyl-piperidin-1-yl)-2-hydroxy-3-oxo-propyl]-carbamic acid tert-butyl ester

carbonic acid 1-{N-benzyl-N'-[(2,6-dimethyl-phenoxy)-acetyl]-hydrazinocarbonyl}-2-tert-butoxycarbonylamino-3-phenyl-propyl ester isobutyl ester

Refernces

• 1、 Richter, Anja,Hedberg, Christian. "A practical and convenient synthesis of the protease inhibitor epibestatin". experimental part. p. 2039 - 2042. Retrieved 2010/08/13.
• 2、 -. "PROCESS FOR PRODUCING 3-AMINO-2-HYDROXYPROPIONIC ACID DERIVATIVES". . . Retrieved 2008/06/13.