(R)-2-(((Benzyloxy)carbonyl)amino)-4-phenylbutanoic acid

Base Information

• Chemical Name: (R)-2-(((Benzyloxy)carbonyl)amino)-4-phenylbutanoic acid
• CAS No.: 138812-70-1
• Molecular Formula: C18H19NO4
• Molecular Weight: 313.353
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID40426927
• Wikidata: Q72502127
• Mol file: 138812-70-1.mol

Synonyms:138812-70-1;(R)-2-(((Benzyloxy)carbonyl)amino)-4-phenylbutanoic acid;Z-D-HOMOPHE-OH;Cbz-D-homoPhenylalanine;Cbz-D-homophenyl-Ala;(2R)-4-phenyl-2-(phenylmethoxycarbonylamino)butanoic acid;Z-D-homophenylalanine;Cbz-D-Homophe;SCHEMBL1796250;BDBM36224;DTXSID40426927;(2R)-2-{[(benzyloxy)carbonyl]amino}-4-phenylbutanoic acid;MFCD00066107;AKOS015911471;AM83540;BS-21377;CS-0445791;EN300-6747824;(R)-2-(benzyloxycarbonylamino)-4-phenylbutanoic acid

Chemical Property of (R)-2-(((Benzyloxy)carbonyl)amino)-4-phenylbutanoic acid

Chemical Property:

• Melting Point: 103 - 104 °C
• PSA: 75.63000
• LogP: 3.38970
• Storage Temp.: Store at RT.
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 8
• Exact Mass: 313.13140809
• Heavy Atom Count: 23
• Complexity: 373

Purity/Quality:

99% ^*data from raw suppliers

Z-D-homophenylalanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CCC(C(=O)O)NC(=O)OCC2=CC=CC=C2
• Isomeric SMILES: C1=CC=C(C=C1)CC[C@H](C(=O)O)NC(=O)OCC2=CC=CC=C2
• Uses: Z-D-Homophe-oh is a useful intermediate used in the synthesis of rapamycin-peptide hybrid molecules that functions as macrocyclic immunosuppressants.

Technology Process of (R)-2-(((Benzyloxy)carbonyl)amino)-4-phenylbutanoic acid

There total 13 articles about (R)-2-(((Benzyloxy)carbonyl)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:

methyl (2S)-2-{[(benzyloxy)carbonyl]amino}-4-phenylbutanoate (142037-77-2) → Z-homophenylalanine (83793-44-6,127862-89-9,135911-27-2,138812-70-1)

Guidance literature:

With lithium hydroxide; In methanol; water; at 0 - 20 ℃; for 8h;

DOI:10.1016/j.bmc.2015.09.029

Reference yield:

N-(Benzyloxycarbonyloxy)succinimide (13139-17-8) + D-homophenylalanine (82795-51-5) → Cbz-D-homoPhe-OH (138812-70-1)

Guidance literature:

With triethylamine; In tetrahydrofuran; water; at 20 ℃;

Reference yield:

benzyl (4R)-2,2-dimethyl-4-(2-phenylethyl)-1,3-oxazolidine-3-carboxylate (412917-36-3) → Cbz-D-homoPhe-OH (138812-70-1)

Guidance literature:

With jones reagent; In acetone; at 0 - 20 ℃; for 4h;

DOI:10.1021/jo010865a

upstream raw materials:

(2S)-2-benzyloxycarbonylamino-4-phenylbutyric acid ethyl ester

benzyl chloroformate

L-(+)-α-amino-4-phenylbutyric acid ethyl ester hydrochloride

D-homophenylalanine

Downstream raw materials:

C₃₁H₃₃ClN₂O₆

2-(benzyloxycarbonylamino)-N-[2-benzoyl-6-(4-(tert-butoxycarbonyl)piperazin-1-yl)phenyl]-4-phenylbutanamide

2-(benzyloxycarbonylamino)-N-[2-benzoyl-6-(4-(tert-butoxycarbonyl)piperazin-1-yl)phenyl]-4-phenylbutanamide

N-(benzyloxycarbonyl)-homo-L-phenylalaninal

Refernces

• 1、 -. "COMPOUNDS AND COMPOSITIONS AS CHANNEL ACTlVATING PROTEASE INHIBITORS". Page/Page column 24-25. . Retrieved 2008/12/08.
• 2、 Collier, Philip N.,Campbell, Andrew D.,Patel, Ian,Raynham, Tony M.,Taylor, Richard J. K.. "Enantiomerically pure α-amino acid synthesis via hydroboration - Suzuki cross-coupling". . p. 1802 - 1815. Retrieved 2007/10/03.