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N-Boc-N'-Cbz-L-lysine

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CAS:2389-45-9
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  • CAS:2389-45-9
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  • 2024-06-13
  • CAS:2389-45-9
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N-Boc-N'-Cbz-L-lysine Basic information
Product Name:N-Boc-N'-Cbz-L-lysine
Synonyms:N6-Benzyloxycarbonyl-N2-tert-butoxycarbonyl-L-lysine;2-(tert-Butoxycarbonylamino)-6-(benzoxycarbonylamino)hexanoic acid;BOC-Z-LYSINE;BOC-N-E-Z-L-LYSINE;N-tert-Butoxycarbonyl-Nε-Cbz-L-lysine;NALPHA-BOC-NEPSILON-CBZ-L-LYSINE;NALPHA-BOC-NEPSILON-Z-L-LYSINE;N-ALPHA-T-BUTYLOXYCARBONYL-N-EPSILON-BENZYLOXYCARBONYL-L-LYSINE
CAS:2389-45-9
MF:C19H28N2O6
MW:380.44
EINECS:219-221-0
Product Categories:Boc-Amino acid series;Lysine [Lys, K];Boc-Amino Acids and Derivative;Amino Acids (N-Protected);Biochemistry;Boc-Amino Acids;Cbz-Amino Acids;Amino Acid Derivatives;Amino Acids
Mol File:2389-45-9.mol
N-Boc-N'-Cbz-L-lysine Structure
N-Boc-N'-Cbz-L-lysine Chemical Properties
Melting point 75.0 to 79.0 °C
Boiling point 587.0±50.0 °C(Predicted)
density 1.176±0.06 g/cm3(Predicted)
refractive index -8 ° (C=2.5, AcOH)
storage temp. Sealed in dry,Store in freezer, under -20°C
solubility almost transparency in Acetic acid
pka3.99±0.21(Predicted)
form powder to crystal
color White to Almost white
BRN 1917222
InChIKeyBDHUTRNYBGWPBL-HNNXBMFYSA-N
SMILESC(O)(=O)[C@H](CCCCNC(OCC1=CC=CC=C1)=O)NC(OC(C)(C)C)=O
CAS DataBase Reference2389-45-9(CAS DataBase Reference)
EPA Substance Registry SystemN2-tert-Butoxycarbonyl-N6-benzyloxycarbonyl lysine (2389-45-9)
Safety Information
Safety Statements 24/25
WGK Germany 3
TSCA Yes
HS Code 2924 29 70
MSDS Information
ProviderLanguage
SigmaAldrich English
N-Boc-N'-Cbz-L-lysine Usage And Synthesis
UsesBoc-Lys(Z)-OH, is used in the synthesis of Isodesmosine Chloride (I815050), which is a component of elastin.
reaction suitabilityreaction type: Boc solid-phase peptide synthesis
Synthesis
N-(Benzyloxycarbonyloxy)succinimide

13139-17-8

Boc-Lys-OH

13734-28-6

N-Boc-N'-Cbz-L-lysine

2389-45-9

The general procedure for the synthesis of N-Boc-N'-Cbz-L-lysine from N-alpha-Boc-L-lysine and phenylmethoxycarbonylsuccinimide was as follows: to a mixed solution of (2S)-6-amino-2-(tert-butoxycarbonylamino)hexanoic acid (100.00 g, 406.01 mmol, 1.00 equiv) and NaHCO3 (102.33 g 1.22 mol, 3.00 eq.) in a mixed solution of THF (1000 mL) and water (1000 mL) was slowly added CbzOSu (101.19 g, 406.01 mmol, 1.00 eq.) at 0 °C. Subsequently, the reaction mixture was stirred at 30 °C for 16 hours. Upon completion of the reaction, the pH of the reaction mixture was adjusted to 5-6 with 1N HCl and then extracted with ethyl acetate (600 mL x 3). The organic phases were combined, dried with anhydrous Na2SO4 and concentrated under reduced pressure to afford the target product (2S)-6-(benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino)hexanoic acid (142.00 g, 373.26 mmol, 91.9% yield) as a yellow oil.

References[1] Patent: US2016/96830, 2016, A1. Location in patent: Paragraph 0368-0369
Tag:N-Boc-N'-Cbz-L-lysine(2389-45-9) Related Product Information
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