Z-Asn-OtBu

Base Information

• Chemical Name: Z-Asn-OtBu
• CAS No.: 25456-85-3
• Molecular Formula: C16H22N2O5
• Molecular Weight: 322.361
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID70426753
• Wikidata: Q82239574
• Mol file: 25456-85-3.mol

Synonyms:Z-Asn-OtBu;25456-85-3;Z-L-asparagine tert-butyl ester;tert-butyl (2S)-4-amino-4-oxo-2-(phenylmethoxycarbonylamino)butanoate;SCHEMBL6078490;DTXSID70426753;CHLOOSRSKMKBDP-LBPRGKRZSA-N;MFCD00056253;AKOS024386419;FD21187;AS-48992;N-carbobenzyloxyasparagine tert-butyl ester;CS-0204264;tert-butyl ((benzyloxy)carbonyl)-L-asparaginate;J-016000;(S)-tert-butyl 4-amino-2-(benzyloxycarbonylamino)-4-oxobutanoate

Chemical Property of Z-Asn-OtBu

Chemical Property:

• Boiling Point: 542 °C at 760 mmHg
• PKA: 10.70±0.46(Predicted)
• Flash Point: 281.6 °C
• PSA: 107.72000
• Density: 1.188 g/cm³
• LogP: 2.58970
• Storage Temp.: -15°C
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 9
• Exact Mass: 322.15287181
• Heavy Atom Count: 23
• Complexity: 425

Purity/Quality:

99% ^*data from raw suppliers

N-α-Z-L-Asparaginetert-ButylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Z-Asn-OtBu

There total 8 articles about Z-Asn-OtBu 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:

N-(benzyloxycarbonyl)-3-cyano-L-alanine (3309-41-9) + isobutene (115-11-7,15220-85-6) → (S)-N-benzyloxycarbonylaspargine t-butyl ester (25456-85-3)

Guidance literature:

With sulfuric acid; In dichloromethane;

DOI:10.1021/ja00885a020

Reference yield:

(S)-tert-butyl isoxazolidine-3-carboxylate (78266-75-8) → (S)-N-benzyloxycarbonylaspargine t-butyl ester (25456-85-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.75 g / hydrogen / 5percent Rh/C / ethanol / 20 h / Ambient temperature

2: 79 percent / 1 M NaHCO₃, 1 M Na₂CO₃ / CHCl₃ / 5 h / Ambient temperature

3: 84 percent / KMnO₄ / acetone; acetic acid / 3.5 h / Ambient temperature

4: 1.) N-methylmorpholine, isobutyl chloroformate; 2.) NH₃ / 1.) THF, 7 min, -20 deg C; 2.) water, 2 h, -15 -> 10 deg C

With 4-methyl-morpholine; potassium permanganate; ammonia; hydrogen; sodium hydrogencarbonate; sodium carbonate; isobutyl chloroformate; Rh on carbon; In ethanol; chloroform; acetic acid; acetone;

DOI:10.1002/hlca.19830660424

Reference yield:

t-butyl (3S)-2-(2,3:5,6-di-O-isopropylidene-α-D-mannofuranosyl)-3-isoxazolidinecarboxylate (78266-73-6) → (S)-N-benzyloxycarbonylaspargine t-butyl ester (25456-85-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 90 percent / 36percent HCl / H₂O; methanol / 6 h / Ambient temperature

2: 1.75 g / hydrogen / 5percent Rh/C / ethanol / 20 h / Ambient temperature

3: 79 percent / 1 M NaHCO₃, 1 M Na₂CO₃ / CHCl₃ / 5 h / Ambient temperature

4: 84 percent / KMnO₄ / acetone; acetic acid / 3.5 h / Ambient temperature

5: 1.) N-methylmorpholine, isobutyl chloroformate; 2.) NH₃ / 1.) THF, 7 min, -20 deg C; 2.) water, 2 h, -15 -> 10 deg C

With 4-methyl-morpholine; hydrogenchloride; potassium permanganate; ammonia; hydrogen; sodium hydrogencarbonate; sodium carbonate; isobutyl chloroformate; Rh on carbon; In methanol; ethanol; chloroform; water; acetic acid; acetone;

DOI:10.1002/hlca.19830660424

upstream raw materials:

N-(benzyloxycarbonyl)-3-cyano-L-alanine

isobutene

(S)-2-benzyloxycarbonylamino-succinic acid 1-tert-butyl ester

N-benzyloxycarbonyl-L-asparagine

Downstream raw materials:

(S)-2-[(R)-2-(Trityl-amino)-3-tritylsulfanyl-propionylamino]-succinamic acid tert-butyl ester

N-benzyloxycarbonyl-L-asparagine

(S)-2-Amino-succinamic acid tert-butyl ester; compound with toluene-4-sulfonic acid

L-asparagine tert-butyl ester

Refernces

• 1、 Galpin,Hancock,Kenner. "The synthesis of an insulin active site analogue". . p. 149 - 158. Retrieved 2007/10/02.