(R)-3-(((Benzyloxy)carbonyl)amino)-4-methylpentanoic acid

Base Information

• Chemical Name: (R)-3-(((Benzyloxy)carbonyl)amino)-4-methylpentanoic acid
• CAS No.: 215608-32-5
• Molecular Formula: C14H19NO4
• Molecular Weight: 265.309
• DSSTox Substance ID: DTXSID40514454
• Nikkaji Number: J1.374.266I
• Wikidata: Q82374796
• Mol file: 215608-32-5.mol

Synonyms:215608-32-5;(R)-3-(((Benzyloxy)carbonyl)amino)-4-methylpentanoic acid;CBZ-D-BETA-HOMOVALINE;(3R)-4-methyl-3-(phenylmethoxycarbonylamino)pentanoic acid;(3R)-3-{[(Benzyloxy)carbonyl]amino}-4-methylpentanoic acid;(R)-3-(((Benzyloxy)carbonyl)amino)-4-methylpentanoicacid;MFCD18252689;SCHEMBL19859590;DTXSID40514454;AKOS026670183;AS-37868;CS-0171631;EN300-816483;A912261

Chemical Property of (R)-3-(((Benzyloxy)carbonyl)amino)-4-methylpentanoic acid

Chemical Property:

• PSA: 79.12000
• LogP: 2.61650
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 7
• Exact Mass: 265.13140809
• Heavy Atom Count: 19
• Complexity: 298

Purity/Quality:

99% ^*data from raw suppliers

(R)-3-(((Benzyloxy)carbonyl)amino)-4-methylpentanoicacid 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C(CC(=O)O)NC(=O)OCC1=CC=CC=C1
• Isomeric SMILES: CC(C)[C@@H](CC(=O)O)NC(=O)OCC1=CC=CC=C1

Technology Process of (R)-3-(((Benzyloxy)carbonyl)amino)-4-methylpentanoic acid

There total 16 articles about (R)-3-(((Benzyloxy)carbonyl)amino)-4-methylpentanoic 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: 96.0%

benzyl (S)-(1-diazo-4-methyl-2-oxopentan-3-yl)carbamate (90105-46-7,28094-73-7) → (R)-3-<(benzyoxycarbonyl)amino>-4-methylpentanoic acid (215608-32-5)

Guidance literature:

With silver trifluoroacetate; silica gel; In ethyl acetate; at 50 ℃; for 0.25h;

DOI:10.1080/00397910500290466

Reference yield: 86.0%

{(R)-2-Methyl-1-[2-oxo-2-((1R,2R,4R)-1,7,7-trimethyl-2-trimethylsilanyloxy-bicyclo[2.2.1]hept-2-yl)-ethyl]-propyl}-carbamic acid benzyl ester (271600-14-7) → (R)-3-<(benzyoxycarbonyl)amino>-4-methylpentanoic acid (215608-32-5)

Guidance literature:

With ammonium cerium(IV) nitrate; In acetonitrile; at 0 ℃; for 16h;

DOI:10.1002/(SICI)1521-3773(20000317)39:6<1063::AID-ANIE1063>3.0.CO;2-Y

Reference yield: 80.0%

silver benzoate (532-31-0) + benzyl (S)-(1-diazo-4-methyl-2-oxopentan-3-yl)carbamate (90105-46-7,28094-73-7) → (R)-3-<(benzyoxycarbonyl)amino>-4-methylpentanoic acid (215608-32-5)

Guidance literature:

In 1,4-dioxane; water; for 6h; Reflux;

DOI:10.1016/j.tet.2014.05.098

upstream raw materials:

(R)-3-amino-4-methylpentanoic acid

benzyl chloroformate

benzyl (S)-(1-diazo-4-methyl-2-oxopentan-3-yl)carbamate

{(R)-2-Methyl-1-[2-oxo-2-((1R,2R,4R)-1,7,7-trimethyl-2-trimethylsilanyloxy-bicyclo[2.2.1]hept-2-yl)-ethyl]-propyl}-carbamic acid benzyl ester

Downstream raw materials:

methyl (2S,3'R)-2-(3-benzyloxycarbonylamino-4-methylpentanoylamino)-4-methylpentanoate

1-((R)-1-((((2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl)(methyl)amino)-4-methylpentan-3-yl)-3-(4-(tert-butyl)phenyl)urea

(R)-3-(benzyloxycarbonylamino)-4-methylpentanal

1-((R)-1-((((3aR,4R,6R,6aR)-6-(6-amino-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl)(methyl)amino)-4-methylpentan-3-yl)-3-(4-(tert-butyl)phenyl)urea

Refernces

• 1、 Pinho, Vagner D.,Gutmann, Bernhard,Kappe, C. Oliver. "Continuous flow synthesis of β-amino acids from α-amino acids via Arndt-Eistert homologation". . p. 37419 - 37422. Retrieved 2014/12/09.
• 2、 -. "MODULATORS OF HISTONE METHYLTRANSFERASE, AND METHODS OF USE THEREOF". Page/Page column 171-172. . Retrieved 2012/06/30.