Cbz-D-valine

Base Information

• Chemical Name: Cbz-D-valine
• CAS No.: 1685-33-2
• Molecular Formula: C13H17NO4
• Molecular Weight: 251.282
• Hs Code.: 29225090
• European Community (EC) Number: 861-721-1
• UNII: WRJ5TH8NR7
• Nikkaji Number: J232.239K
• Wikidata: Q106902931
• Mol file: 1685-33-2.mol

Synonyms:1685-33-2;CBZ-D-VALINE;Z-D-Val-OH;N-Benzyloxycarbonyl-D-valine;Cbz-D-Val-OH;N-Cbz-D-valine;N-Carbobenzoxy-D-valine;D-Valine, N-[(phenylmethoxy)carbonyl]-;(2R)-3-methyl-2-(phenylmethoxycarbonylamino)butanoic acid;Z-D-Valine;(2R)-2-{[(benzyloxy)carbonyl]amino}-3-methylbutanoic acid;(2R)-2-[[(Benzyloxy)carbonyl]amino]-3-methylbutanoic acid;MFCD00065703;WRJ5TH8NR7;n-benzyloxycarbonyl d-valine;SCHEMBL2978398;((Benzyloxy)carbonyl)-D-valine;CANZBRDGRHNSGZ-LLVKDONJSA-N;N-[(benzyloxy)carbonyl]-D-valine;N-[(benzyloxy) carbonyl]-D-valine;CCG-46181;N-[(Phenylmethoxy)carbonyl]-D-valine;AKOS015924216;AM82370;CS-W014621;HY-W013905;AS-12746;Valine, N-carboxy-, N-benzyl ester, D-;C2139;EN300-121305;A810980;(R)-2-benzyloxycarbonylamino-3-methyl-butyric acid;J-300299;N-alpha-BenZyloxycarbonyl-D-valine (CbZ-D-Val-OH);Q-101853;SR-01000635893-1;(R)-2-(benzyloxycarbonylamino)-3-methylbutanoic acid;(2R)-2-{[(Benzyloxy)carbonyl]amino}-3-methylbutanoic acid, AldrichCPR

Chemical Property of Cbz-D-valine

Chemical Property:

• Vapor Pressure: 2.99E-08mmHg at 25°C
• Melting Point: 58-60 ºC
• Refractive Index: 4 ° (C=2, AcOH)
• Boiling Point: 432.6 ºC at 760 mmHg
• PKA: 4.00±0.10(Predicted)
• Flash Point: 215.4 ºC
• PSA: 75.63000
• Density: 1.182 g/cm³
• LogP: 2.41290
• Storage Temp.: Store at RT.
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 251.11575802
• Heavy Atom Count: 18
• Complexity: 285

Purity/Quality:

99% ^*data from raw suppliers

Z-D-valine 99+% ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C(C(=O)O)NC(=O)OCC1=CC=CC=C1
• Isomeric SMILES: CC(C)[C@H](C(=O)O)NC(=O)OCC1=CC=CC=C1
• Uses: N-Cbz-D-valine is the N-Cbz-protected form of D-Valine (V094200). D-Valine (an isomer of the essential amino acid L-Valine [V094205])exhibited inhibitory effects on fibroblasts that contaminated mammalian kidney cultures, allowing for selective growth epithelial cells. D-Valine is also known for its presence in the structure of Actinomycin D, an antitumour drug. D-Valine is naturally synthesized by Streptomyces antibioticus.

Technology Process of Cbz-D-valine

There total 31 articles about Cbz-D-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: 97.0%

tert-butyl 2-(((benzyloxy)carbonyl)amino)-3-methylbutanoate (20314-88-9) → N-benzyloxycarbonylvaline (1149-26-4,1685-33-2,92077-76-4,3588-63-4)

Guidance literature:

With ytterbium(III) triflate; In nitromethane; at 45 - 50 ℃; for 5h;

Reference yield: 94.0%

2-(((benzyloxy)carbonyl)amino)-3-methylbut-2-enoic acid (95863-98-2) → N-[(benzyloxy)carbonyl]-D-valine (1685-33-2)

Guidance literature:

With hydrogen; triethylamine; (-)-2,2',5,5'-tetramethyl-4,4'-bis(diphenylphosphino)-3,3'-bithiophene; [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; In ethanol; 1,2-dichloro-ethane; at 25 ℃; for 24h; under 4654.33 Torr;

DOI:10.1021/ol050869s

Reference yield: 93.0%

D-Val-OH (640-68-6,25609-85-2,7004-03-7,921-10-8) + benzyl chloroformate (501-53-1,94274-21-2) → N-[(benzyloxy)carbonyl]-D-valine (1685-33-2)

Guidance literature:

With sodium hydrogencarbonate;

DOI:10.1016/S0040-4039(00)01409-X

upstream raw materials:

D,L-valine

benzyl chloroformate

3,5-dimethyl-pyrazole-1-carboxylic acid benzyl ester

tert-butyl 2-(((benzyloxy)carbonyl)amino)-3-methylbutanoate

Downstream raw materials:

N-(N-benzyloxycarbonyl-valyl)-alanine ethyl ester

N-(N-benzyloxycarbonyl-valyl)-thioglycine S-phenyl ester

methyl (S)-2-((S)-2-benzyloxycarbonyl-amino-3-methylbutyrylamino)-3-methylbutyrate

N-benzyloxycarbonyl-D-valyl-L-valine methyl ester

Refernces

• 1、 Cudic, Mare,Mari, Frank,Fields, Gregg B.. "Synthesis and solid-phase application of suitably protected γ-hydroxyvaline building blocks". . p. 5581 - 5586. Retrieved 2007.
• 2、 Hattori, Tetsutaro,Kitamoto, Yuichi,Maeda, Tetsuya,Miyoshi, Ikuko,Morohashi, Naoya. "Enantioselective inclusion of pyrene-1-sulfonate salts of α-amino acids with crystals of α-cyclodextrin". . . Retrieved 2020/04/01.
• 3、 Ramsis, Triveena M.,Abdel Karim, Shereen E.,Vassilaki, Niki,Frakolaki, Efseveia,Kamal, Ahmed A. M.,Zoidis, Grigoris,Ahmed, Nermin S.,Abadi, Ashraf H.. "Expanding the chemical space of anti-HCV NS5A inhibitors by stereochemical exchange and peptidomimetic approaches". . . Retrieved 2018/05/30.