(2S,3R)-3-(Boc-amino)-2-hydroxy-4-phenylbutyric acid

Base Information

• Chemical Name: (2S,3R)-3-(Boc-amino)-2-hydroxy-4-phenylbutyric acid
• CAS No.: 62023-65-8
• Molecular Formula: C15H21NO5
• Molecular Weight: 295.335
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID40444505
• Nikkaji Number: J1.937.693A
• Wikidata: Q82262656
• Mol file: 62023-65-8.mol

Synonyms:62023-65-8;(2S,3R)-3-(Boc-amino)-2-hydroxy-4-phenylbutyric acid;N-Boc-(2S,3R)-2-hydroxy-3-amino-4-phenylbutanoic acid;(2S,3R)-3-((tert-Butoxycarbonyl)amino)-2-hydroxy-4-phenylbutanoic acid;Boc-(2S,3R)-AHPA;(2S,3R)-2-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]-4-phenylbutanoic acid;(2S,3R)-3-{[(tert-butoxy)carbonyl]amino}-2-hydroxy-4-phenylbutanoic acid;MFCD00057841;SCHEMBL825622;DTXSID40444505;AKOS016843855;AS-72743;CS-0134071;EN300-12447022;(2S,3R)-2-Hydroxy-3-(tert-butoxycarbonylamino)-4-phenylbutanoic acid;(2S,3R)-3-((tert-Butoxycarbonyl)amino)-2-hydroxy-4-phenylbutanoicacid;(2S,3R)-3-(Boc-amino)-2-hydroxy-4-phenylbutyric acid, >=98.0% (TLC);(2S,3R)-3-(tert-butoxycarbonylamino)-2-hydroxy-4-phenylbutanoic acid

Chemical Property of (2S,3R)-3-(Boc-amino)-2-hydroxy-4-phenylbutyric acid

Chemical Property:

• Boiling Point: 499.1±45.0 °C(Predicted)
• PKA: 3.57±0.17(Predicted)
• PSA: 95.86000
• Density: 1 +-.0.06 g/cm3(Predicted)
• LogP: 1.95880
• Storage Temp.: −20°C
• Water Solubility.: Insoluble in water. Soluble in organic solvents.
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 295.14197277
• Heavy Atom Count: 21
• Complexity: 358

Purity/Quality:

99.5% ^*data from raw suppliers

(2S,3R)-3-(Boc-amino)-2-hydroxy-4-phenylbutyric acid ≥98.0% (TLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CC1=CC=CC=C1)C(C(=O)O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@H](CC1=CC=CC=C1)[C@@H](C(=O)O)O
• Uses: (2S,3R)-3-(Boc-amino)-2-hydroxy-4-phenylbutyric acid, is used as a novel protected amino acid for the preparation of bestatin and analogs.

Technology Process of (2S,3R)-3-(Boc-amino)-2-hydroxy-4-phenylbutyric acid

There total 44 articles about (2S,3R)-3-(Boc-amino)-2-hydroxy-4-phenylbutyric 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%

di-tert-butyl dicarbonate (24424-99-5) + (2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid (59554-14-2) → (2S,3R)-3-[(tert-butoxycarbonyl) amino]-2-hydroxy-4-phenyl-butanoic acid (62023-65-8)

Guidance literature:

With potassium carbonate; In tetrahydrofuran; water; at 0 - 20 ℃; for 1h;

Reference yield: 79.0%

N-(tert-butyloxycarbonyl)-(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid methyl ester (81926-51-4) → (2S,3R)-3-[(tert-butoxycarbonyl) amino]-2-hydroxy-4-phenyl-butanoic acid (62023-65-8)

Guidance literature:

With sodium carbonate; In methanol; water; at 20 ℃; for 12h;

DOI:10.1016/S0040-4039(03)01799-4

Reference yield: 45.0%

sodium cyanide (773837-37-9) + di-tert-butyl dicarbonate (24424-99-5) + Boc-D-Phe-OH (18942-49-9) → (2S,3R)-3-[(tert-butoxycarbonyl) amino]-2-hydroxy-4-phenyl-butanoic acid (62023-65-8)

Guidance literature:

Boc-D-Phe-OH; With sodium hydrogensulfite; In water; ethyl acetate; for 10h;

sodium cyanide; In water; ethyl acetate; at 20 ℃;

di-tert-butyl dicarbonate;

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

(S)-2-{[(R)-3-((2S,3S)-3-tert-Butoxycarbonylamino-2-hydroxy-4-phenyl-butyryl)-thiazolidine-4-carbonyl]-amino}-3-methyl-butyric acid methyl ester

(S)-2-{[(R)-3-((2S,3S)-3-tert-Butoxycarbonylamino-2-hydroxy-4-phenyl-butyryl)-5,5-dimethyl-thiazolidine-4-carbonyl]-amino}-3-methyl-butyric acid methyl ester

(S)-2-((S)-3-Amino-2-oxo-4-phenyl-butyrylamino)-4-methyl-pentanoic acid; compound with trifluoro-acetic acid

Refernces

• 1、 Yang, Yun-kai,Shen, Da-dong,He, Peng,Du, Liang-dong,Wan, Ding-jian,Wang, Pu,Wang, Tao,Feng, Mei-qing. "Chemically synthesized LYRM03 could inhibit the metastasis of human breast cancer MDA-MB-231 cells in vitro and in vivo". . p. 1719 - 1726. Retrieved 2019.
• 2、 -. "A synthesis method of ubenimex". Paragraph 0016; 0025; 0026; 0027-0030; 0036-0041; 0047-0052. . Retrieved 2017/05/19.