Cbz-N-methyl-L-valine

Base Information

• Chemical Name: Cbz-N-methyl-L-valine
• CAS No.: 42417-65-2
• Molecular Formula: C14H19NO4
• Molecular Weight: 265.309
• Hs Code.: 2922509090
• European Community (EC) Number: 610-027-5
• DSSTox Substance ID: DTXSID00426827
• Nikkaji Number: J494.842D
• Wikidata: Q72516320
• Mol file: 42417-65-2.mol

Synonyms:(S)-N-(Benzyloxycarbonyl)-N-methylvaline;N-(Benzyloxycarbonyl)-N-methylvaline;Cbz-N-Me-Val-OH;

Chemical Property of Cbz-N-methyl-L-valine

Chemical Property:

• Vapor Pressure: 2.34E-07mmHg at 25°C
• Melting Point: 68-70 °C(lit.)
• Refractive Index: 1.532
• Boiling Point: 407.1 °C at 760 mmHg
• PKA: 4.01±0.10(Predicted)
• Flash Point: 200 °C
• PSA: 66.84000
• Density: 1.167 g/cm³
• LogP: 2.36420
• Storage Temp.: Store at RT.
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Ethanol (Slightly), Methanol (Slightly)
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 265.13140809
• Heavy Atom Count: 19
• Complexity: 311

Purity/Quality:

98% ^*data from raw suppliers

Z-N-methyl-L-valine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 36/37

MSDS Files:

Useful:

• Canonical SMILES: CC(C)C(C(=O)O)N(C)C(=O)OCC1=CC=CC=C1
• Isomeric SMILES: CC(C)[C@@H](C(=O)O)N(C)C(=O)OCC1=CC=CC=C1
• Uses: (S)-N-(Benzyloxycarbonyl)-N-methylvaline has been used as a reactant in the synthesis of a biologically active cyclodepsipeptide destruxin E which is a potent negative regulator of osteoclast morphology.

Technology Process of Cbz-N-methyl-L-valine

There total 10 articles about Cbz-N-methyl-L-valine 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: 92.0%

(4S)-4-isopropyl-5-oxo-1,3-oxazolidine-3-carboxylic acid benzyl ester (66866-64-6) → Z-MeVal-OH (42417-65-2)

Guidance literature:

With chloro-trimethyl-silane; sodium cyanoborohydride; In acetonitrile; for 0.166667h; Ambient temperature;

DOI:10.1246/cl.1999.299

Reference yield: 78.0%

(S)-N-(benzyloxycarbonyl)valine (1149-26-4) + methyl iodide (74-88-4) → Z-MeVal-OH (42417-65-2)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 20 ℃; for 24h;

DOI:10.7164/antibiotics.55.322

Reference yield:

(S)-N-(benzyloxycarbonyl)valine (1149-26-4) → Z-MeVal-OH (42417-65-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / CSA / toluene / Heating

2: Et₃SiH; CF₃COOH / CH₂Cl₂

With triethylsilane; trifluoroacetic acid; camphor-10-sulfonic acid; In dichloromethane; toluene;

DOI:10.1002/hlca.200690235

upstream raw materials:

N-Me-Cbz-valine

N-methyl-L-valine

benzyl chloroformate

(S)-N-(benzyloxycarbonyl)valine

Downstream raw materials:

N-Benzyloxycarbonyl-N-methyl-L-Val-D-α-hydroxy-isovaleriansaeure

(3S)-4-methyl-3-(methyl{[(phenylmethyl)oxy]carbonyl}amino)pentanoic acid

N-benzyloxycarbonyl-N-methyl-L-valine N-hydroxysuccinimide ester

methyl (2S)-3-methyl-[(benzyloxy)carbonylamino]butanoate

Refernces

• 1、 Hughes, Andrew B.,Sleebs, Brad E.. "Synthesis of new β-amino acids via 5-oxazolidinones and the arndt-eistert procedure". . p. 778 - 784. Retrieved 2007/10/03.
• 2、 Hasuoka, Atsushi,Nishikimi, Yuji,Nakayama, Yutaka,Kamiyama, Keiji,Nakao, Masafumi,Miyagawa, Ken-Ichiro,Nishimura, Osamu,Fujino, Masahiko. "Synthesis and anti-Helicobacter pylori activity of pyloricidin derivatives. I. Structure-activity relationships on the terminal peptidic moiety". . p. 322 - 336. Retrieved 2007/10/03.