(S)-2-(((Benzyloxy)carbonyl)amino)pentanoic acid
Basic information
- CAS
21691-44-1- Standard SMILES
CCC[C@H](NC(=O)OCc1ccccc1)C(=O)O- InChIKey
NSJDRLWFFAWSFP-NSHDSACASA-N- Molecular formula
- C13H17NO4
- Average molar mass
- 251.28 g/mol
- Monoisotopic mass
- 251.11575802
Names & identifiers
- Preferred name
- (S)-2-(((Benzyloxy)carbonyl)amino)pentanoic acid
- IUPAC
- (2S)-2-(phenylmethoxycarbonylamino)pentanoic acid
- English name
- Z-Nva-OH
- Molecular formula
- C13H17NO4
- Molecular weight
- 251.28
Names & synonyms
Z-Nva-OH21691-44-1(S)-2-(((Benzyloxy)carbonyl)amino)pentanoic acidCbz-L-NorvalineZ-L-norvaline(2S)-2-(phenylmethoxycarbonylamino)pentanoic acidMFCD00063167(2S)-2-{[(benzyloxy)carbonyl]amino}pentanoic acidSCHEMBL265461DS-16711N-CBZ-L-NORVALINE(2S)-2-(((benzyloxy)carbonyl)aMino)pentanoic acid
Show more names
N-Carbobenzoxy-DL-norvalineCbz-Nva-OHZ-L-Nva-OHZ-APE(2)-OHZ-NORVALINECBZ-L-NVA-OHZ-Nva-OH ,98%
Z-L--aminovaleric acidValaciclovir Impurity 35benzyl-oxycarbonyl-l-norvalibenzyl-oxycarbonyl-l-norvalinen-benzyloxycarbonyl-l-norvalineDTXSID10426353NSJDRLWFFAWSFP-NSHDSACASA-NN-[(Benzyloxy)carbonyl]-L-norvaline
Database identifiers
- CAS
21691-44-1- PubChem CID
- 6993399
- DTXSID
DTXSID10426353- Nikkaji
- J231.982I
Properties
Computed structural properties
- XLogP
- 2.3
- Topological polar surface area
- 75.6 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 7
- Heavy atoms
- 18
- Formal charge
- 0
- Complexity
- 274
Physicochemical properties
- Boiling point
- 439.4 · 439.4±38.0 °C(Predicted)
- Density
- 1.184 · 1.184±0.06 g/cm3(Predicted)
- storage temp.
- 2 · Sealed in dry,2-8°C
- solubility
- Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
- form
- Powder
- pka
- 4 · 4.00±0.20(Predicted)
- Appearance
- White to off-white Solid
- CAS DataBase Reference
- 21691 · 21691-44-1(CAS DataBase Reference)
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319-H335
- Precautionary statements
- 271 · P271-P261-P280
- HS Code
- 2922498590 · 2922498590
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- hs_code
- 2922498590
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H315-H319-H335
- Precautionary statements
- P271-P261-P280
Chemistry & industry
Applications
UsesZ-NVA-OH is also known as Cbz-L-norvaline. It could be used to synthesise Z-Nva-Ser(Bu’)-Gly-OPh. In specific steps, as follows: the protected dipeptide(53.1 g. 124mM) and Tos.OH.H2O (33.6g. 124mM) were dissolved in DMF (200) and hydrogenolysed overnight in the presence of 10% Pd/C (6g), then filtered and concentrated to 100ml. Z-Nva-OH (37.4g. 149mM) was dissolved in CH2Cl2 (170ml) and NMM (16.4ml. 149mM) added. After cooling to -20℃, pivaloyl chloride (17.8ml. 145 mM) was added, and the solution was stirred for 20 minutes before the precooled DMF solution from above was added. Following the addition of NMM (13.6 ml, 124 mM), the reaction was stirred at - 20℃ for 3 hr, then maintained at room temperature overnight. The solution was evaporated, and the product dissolved in EtOAc. Washing with acid and base in the usual way, followed by crystallisation from EtOAc/petroleum ether yielded Z-Nva-Ser(Bu’)-Gly-OPh[1].
Upstream & downstream products
Downstream products
Related reactions
1 records
Compound notes
Loading…