6-[(2-Methylpropan-2-yl)oxycarbonylamino]-2-(phenylmethoxycarbonylamino)hexanoic acid

Base Information

• Chemical Name: 6-[(2-Methylpropan-2-yl)oxycarbonylamino]-2-(phenylmethoxycarbonylamino)hexanoic acid
• CAS No.: 2389-60-8
• Molecular Formula: C19H28N2O6
• Molecular Weight: 380.441
• Hs Code.: 29242990
• NSC Number: 164047
• Mol file: 2389-60-8.mol

Synonyms:6-[(2-methylpropan-2-yl)oxycarbonylamino]-2-(phenylmethoxycarbonylamino)hexanoic acid;215595-66-7;Nepsilon-Boc-Nalpha-Cbz-L-lysine;MFCD00062271;MFCD00065699;NSC-164047;NSC164047;N2-Cbz-N6-Boc-D-lysine;N6-Boc-N2-Cbz-DL-lysine;SCHEMBL699636;DYSBKEOCHROEGX-UHFFFAOYSA-N;N-alpha-Z-N-epsilon-Boc-L-lysine;AB02445;2-{[(BENZYLOXY)CARBONYL]AMINO}-6-{[(TERT-BUTOXY)CARBONYL]AMINO}HEXANOIC ACID;SY060104;SY110367;FT-0629719;FT-0629772;A835567;F2191-0247;2-benzyloxycarbonylamino-6-tert-butoxycarbonylamino-hexanoic acid;(2S)-6-[(2-methylpropan-2-yl)oxycarbonylamino]-2-(phenylmethoxycarbonylamino)hexanoic acid;6-[[(2-methylpropan-2-yl)oxy-oxomethyl]amino]-2-(phenylmethoxycarbonylamino)hexanoic acid

Chemical Property of 6-[(2-Methylpropan-2-yl)oxycarbonylamino]-2-(phenylmethoxycarbonylamino)hexanoic acid

Chemical Property:

• Appearance/Colour: White crystals
• Vapor Pressure: 1.26E-14mmHg at 25°C
• Melting Point: 63-70 °C
• Refractive Index: -6 ° (C=1, MeOH)
• Boiling Point: 587 °C at 760 mmHg
• PKA: 3.98±0.21(Predicted)
• Flash Point: 308.8 °C
• PSA: 113.96000
• Density: 1.176 g/cm³
• LogP: 3.84280
• Storage Temp.: 2-8°C
• Solubility.: Soluble in DMF (0.5 mmol/ml).
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 12
• Exact Mass: 380.19473662
• Heavy Atom Count: 27
• Complexity: 483

Purity/Quality:

99% ^*data from raw suppliers

Z-Lys(Boc)-OH ^*data from reagent suppliers

Safty Information:

• Safety Statements: S24/25:Avoid contact with skin and eyes.

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NCCCCC(C(=O)O)NC(=O)OCC1=CC=CC=C1
• Uses: It is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuff fields.

Technology Process of 6-[(2-Methylpropan-2-yl)oxycarbonylamino]-2-(phenylmethoxycarbonylamino)hexanoic acid

There total 17 articles about 6-[(2-Methylpropan-2-yl)oxycarbonylamino]-2-(phenylmethoxycarbonylamino)hexanoic 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: 100.0%

di-tert-butyl dicarbonate (24424-99-5) + N2-[(benzyloxy)carbonyl]-L-lysine (2212-75-1) → Z-Lys(Boc)-OH (2389-60-8)

Guidance literature:

With sodium hydrogencarbonate; In tetrahydrofuran; water; at 20 ℃;

Reference yield: 94.0%

(S)-2-amino-6-(tert-butoxycarbonylamino)hexanoic acid (2418-95-3) + benzyl chloroformate (501-53-1,94274-21-2) → Z-Lys(Boc)-OH (2389-60-8)

Guidance literature:

With aq. alkali;

DOI:10.1021/ja00380a019

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) + tert-butyl 1H-benzo[d][1,2,3]triazole-1-carboxylate (130384-98-4) → Z-Lys(Boc)-OH (2389-60-8)

Guidance literature:

L-Lysine hydrochloride; tert-butyl 1H-benzo[d][1,2,3]triazole-1-carboxylate; With sodium hydroxide; In tetrahydrofuran; water; at 0 ℃; pH=11.5;

benzyl chloroformate; In tetrahydrofuran; water; pH=10 - 11;

With hydrogenchloride; In Isopropyl acetate; water; pH=2;

upstream raw materials:

N-(tert-butyloxycarbonyl) azide

N₂-[(benzyloxy)carbonyl]-L-lysine

tert-butyl fluoroformate

1,1-dimethylethyl 2,4,5-trichlorophenyl carbonate

Downstream raw materials:

3-(N^α-benzyloxycarbonyl-N^ε-t-butoxycarbonyl-lysyl)-1,3-thiazolidine-2-thione

N-(N^α-carbobenzoxy-N^ε-tert-butoxycarbonyl-L-lysyl)glycine ethyl ester

Z-Lys(Boc)-D-Trp-isoamylamide

N^α-benzyloxycarbonyl-N^ε-tert-butyloxycarbonyllysyl-N^ε-tert-butyloxycarbonyllysyl-leucine tert-butyl ester

Refernces

• 1、 Kabes, Connor Q.,Gunn, Jack H.,Selbst, Maximilian A.,Lucas, Reagan F.,Gladysz, John A.. "Syntheses of Enantiopure 1,2-Ethylenediamines with Tethered Secondary Amines of the Formula H 2NCH 2CH[(CH 2) nNHMe]NH 2(n = 1-4) from α-Amino Acids: New Agents for Asymmetric Catalysis". . p. 3277 - 3285. Retrieved 2020/11/02.
• 2、 Kumbhakonam, Sateeshkumar,Vellaisamy, Kasipandi,Saroj, Soumya,Venkatesan, Nalini,Karunagaran,Manheri, Muraleedharan Kannoth. "Serine- and threonine-derived diamine equivalents for site-specific incorporation of platinum centers in peptides, and the anticancer potential of these conjugates". supporting information. p. 2450 - 2458. Retrieved 2018/02/19.