Z-Val-Val-OH

Base Information

• Chemical Name: Z-Val-Val-OH
• CAS No.: 19542-54-2
• Molecular Formula: C18H26 N2 O5
• Molecular Weight: 350.415
• DSSTox Substance ID: DTXSID401258175
• Nikkaji Number: J293.793J
• Mol file: 19542-54-2.mol

Synonyms:Z-Val-Val-OH;19542-54-2;(2S)-3-methyl-2-[[(2S)-3-methyl-2-(phenylmethoxycarbonylamino)butanoyl]amino]butanoic acid;SCHEMBL6272667;DTXSID401258175;N-benzyloxycarbonyl-l-valyl-l-valine;MFCD00191172;N-[(Phenylmethoxy)carbonyl]-L-valyl-L-valine;(S)-2-((S)-2-(benzyloxycarbonylamino)-3-methylbutanamido)-3-methylbutanoic acid

Chemical Property of Z-Val-Val-OH

Chemical Property:

• PSA: 104.73000
• LogP: 2.94460
• Storage Temp.: -15°C
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 9
• Exact Mass: 350.18417193
• Heavy Atom Count: 25
• Complexity: 458

Purity/Quality:

99% ^*data from raw suppliers

Z-VAL-VAL-OH ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Z-Val-Val-OH

There total 16 articles about Z-Val-Val-OH 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: 93.0%

methyl (S)-2-((S)-2-benzyloxycarbonyl-amino-3-methylbutyrylamino)-3-methylbutyrate (1999-88-8) → N-benzyloxycarbonyl-L-valyl-L-valine (19542-54-2)

Guidance literature:

With sodium hydroxide; In acetone; at 20 ℃; for 3h;

DOI:10.1002/ejoc.200400510

Reference yield: 93.0%

2,5-dioxopyrrolidin-1-yl (2S)-2-(((benzyloxy)carbonyl)amino)-3-methylbutanoate (3496-11-5) + L-valine (72-18-4,25609-85-2,7004-03-7,921-10-8) → N-benzyloxycarbonyl-L-valyl-L-valine (19542-54-2)

Guidance literature:

With sodium 2,2,2-trifluoroacetate; triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 2h;

Reference yield: 88.0%

L-valine (72-18-4,25609-85-2,7004-03-7,921-10-8) + Z-Val-ONp (10512-93-3) → N-benzyloxycarbonyl-L-valyl-L-valine (19542-54-2)

Guidance literature:

With sodium hydroxide; In N,N-dimethyl-formamide; at 18 ℃; for 12h;

DOI:10.1007/s11171-005-0029-1

upstream raw materials:

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

Z-Val-Val-OEt

N-Benzyloxycarbonyl-L-valyl-L-valin-4-methoxybenzylester

L-valine

Downstream raw materials:

Z-L-Val-L-Val-L-Glu(OtBu)OtBu

2-(2-{3-[2-(2-amino-3-methylbutyrylamino)-3-methyl-butyrylamino]-2-oxo-pentanoylamino}-4-methylpentanoylamino)-3-methylbutyric acid

2-(2-{3-[2-(2-benzyloxycarbonylamino-3-methylbutyrylamino)-3-methyl-butyrylamino]-2-oxo-pentanoylamino}-4-methylpentanoylamino)-3-methylbutyric acid benzyl ester

Z-Leu-Val-Val-Tyr-Pro

Refernces

• 1、 Spezzacatena, Caterina,Pepe, Antonietta,Green, Lora M.,Sandberg, Lawrence B.,Bochicchio, Brigida,Tamburro, Antonio M.. "Synthesis, solution structure and biological activity of Val-Val-Pro-Gln, a bioactive elastin peptide". . p. 1644 - 1651. Retrieved 2007/10/03.
• 2、 Wasserman, Harry H.,Petersen, Anders K.,Xia, Mingde. "Application of acyl cyanophosphorane methodology to the synthesis of protease inhibitors: Poststatin, eurystatin, phebestin, probestin and bestatin". . p. 6771 - 6784. Retrieved 2007/10/03.