3-Hydroxy-4-[(2-methylpropan-2-yl)oxycarbonylamino]-5-phenylpentanoic acid

Base Information

• Chemical Name: 3-Hydroxy-4-[(2-methylpropan-2-yl)oxycarbonylamino]-5-phenylpentanoic acid
• CAS No.: 72155-46-5
• Molecular Formula: C18H27 N O5
• Molecular Weight: 337.416
• DSSTox Substance ID: DTXSID50405723
• Mol file: 72155-46-5.mol

Synonyms:72155-46-5;Boc-(3S,4S)-AHPPA-OH;3-hydroxy-4-[(2-methylpropan-2-yl)oxycarbonylamino]-5-phenylpentanoic acid;AC1NFQT7;SCHEMBL9832414;DTXSID50405723;FT-0641396;3-hydroxy-4-t-butoxycarbonylamino-5-phenyl pentanoic acid;(3R,4S)-N-(TERT-BUTOXYCARBONYL)-4-AMINO-3-HYDROXY-5-PHENYLPENTANOIC ACID

Chemical Property of 3-Hydroxy-4-[(2-methylpropan-2-yl)oxycarbonylamino]-5-phenylpentanoic acid

Chemical Property:

• PSA: 99.35000
• LogP: 2.16240
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 309.15762283
• Heavy Atom Count: 22
• Complexity: 371

Purity/Quality:

98% ^*data from raw 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(CC(=O)O)O

Technology Process of 3-Hydroxy-4-[(2-methylpropan-2-yl)oxycarbonylamino]-5-phenylpentanoic acid

There total 23 articles about 3-Hydroxy-4-[(2-methylpropan-2-yl)oxycarbonylamino]-5-phenylpentanoic 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: 99.0%

(4S)-4-<(tert-butyloxycarbonyl)amino>-6-methyl-3-oxoheptanoic acid ethyl ester (58521-44-1) → (3S,4S)-ethyl 4-(tert-butoxycarbonylamino)-3-hydroxy-6-methylheptanoate (67010-43-9) + (3S,4S)-4-(N-tert-butoxycarbonyl)amino-3-hydroxy-5-phenylpentanoic acid ethyl ester (72155-46-5)

Guidance literature:

With hydrogen; [(R)-BINAP]RuBr₂; In ethanol; at 18 - 21 ℃; under 76000.1 Torr; Yields of byproduct given; ee = 97percent;

DOI:10.1016/S0040-4039(00)82338-2

Reference yield: 97.0%

(4S)-40<(tertibutyloxycarbonyl)amino>-3-oxo-5-phenylpentanoic acid ethyl ester (112271-08-6) → (3S,4S)-4-(N-tert-butoxycarbonyl)amino-3-hydroxy-5-phenylpentanoic acid ethyl ester (72155-46-5) + N-(tert-butoxycarbonyl)-4(S)-amino-3(R)-hydroxy-5-phenylpentanoic acid ethyl ester (72155-47-6)

Guidance literature:

With hydrogen; (S)-BinapRuBr₂; In ethanol; at 18 - 21 ℃; for 145h; under 76000.1 Torr; Yields of byproduct given; threo/erythro ratio 9/91, ee = 99percent;

DOI:10.1016/S0040-4039(00)82338-2

Reference yield: 97.0%

(4S)-40<(tertibutyloxycarbonyl)amino>-3-oxo-5-phenylpentanoic acid ethyl ester (112271-08-6) → (3S,4S)-4-(N-tert-butoxycarbonyl)amino-3-hydroxy-5-phenylpentanoic acid ethyl ester (72155-46-5)

Guidance literature:

With hydrogen; [(R)-BINAP]RuBr₂; In ethanol; at 20 ℃; for 145h; under 76000.1 Torr;

DOI:10.1248/cpb.38.103

upstream raw materials:

(4S)-40<(tertibutyloxycarbonyl)amino>-3-oxo-5-phenylpentanoic acid ethyl ester

(4S)-4-<(tert-butyloxycarbonyl)amino>-6-methyl-3-oxoheptanoic acid ethyl ester

Boc-L-phenylalaninal

ethyl acetate

Downstream raw materials:

(3S,4S)-4-((3S,4S)-4-((3S,4S)-4-amino-3-hydroxy-6-methylheptanoylamino)-5-cyclohexyl-3-hydroxypentanoylamino)-3-hydroxy-5-phenylpentanoic acid ethyl ester hydrochloride

ES-6864

(3S,4S)-4-amino-5-cyclohexyl-3-hydroxy-N-(2-morpholinoethyl)pentanamide

(3S,4S)-4-((S)-2-Amino-3-thiazol-4-yl-propionylamino)-5-cyclohexyl-3-hydroxy-pentanoic acid (2-morpholin-4-yl-ethyl)-amide