Agaritine

Base Information

• Chemical Name: Agaritine
• CAS No.: 2757-90-6
• Molecular Formula: C12H17 N3 O4
• Molecular Weight: 267.285
• Hs Code.: 2928000090
• UNII: UX8Y7QVP8M
• DSSTox Substance ID: DTXSID9020661
• Nikkaji Number: J15.143B
• Wikipedia: Agaritine
• Wikidata: Q2315302
• Metabolomics Workbench ID: 50037
• Mol file: 2757-90-6.mol

Synonyms:agaritine

Chemical Property of Agaritine

Chemical Property:

• Vapor Pressure: 2.62E-10mmHg at 25°C
• Melting Point: 207°C (rough estimate)
• Refractive Index: 1.5290 (estimate)
• Boiling Point: 487.2°Cat760mmHg
• PKA: 3.4, 8.86(at 25℃)
• Flash Point: 248.5°C
• PSA: 124.68000
• Density: 1.382g/cm³
• LogP: 0.97830
• XLogP3: -2.8
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 267.12190603
• Heavy Atom Count: 19
• Complexity: 303

Purity/Quality:

98%Min ^*data from raw suppliers

Agaritine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Mushroom Toxins
• Canonical SMILES: C1=CC(=CC=C1CO)NNC(=O)CCC(C(=O)O)N
• Isomeric SMILES: C1=CC(=CC=C1CO)NNC(=O)CC[C@@H](C(=O)O)N
• Uses: Agaritine is a carcinogen and an antiviral compound found in mushroom species of the genus Agaricus. Agaritine and related compounds may be potential inhibitors against HIV proteases.

Technology Process of Agaritine

There total 10 articles about Agaritine 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: 82.0%

N2-(benzyloxycarbonyl)-L-glutamic acid 1-(benzyl ester) 5-(2-<4-(hydroxymethyl)phenyl>hydrazide) (71426-48-7) → β-N-[γ-L-(+)glutamyl]-4-(hydroxymethyl)phenylhydrazine (2757-90-6)

Guidance literature:

With hydrogen; Pd/C poisoned with quinoline-sulfur; In methanol; water; for 0.583333h;

DOI:10.1002/hlca.19870700505

Reference yield:

Cbz-(L)-Glu-OBn (3705-42-8) → β-N-[γ-L-(+)glutamyl]-4-(hydroxymethyl)phenylhydrazine (2757-90-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) DCC / 1.) CH₂Cl₂, -10 deg C, 4 h; 2.) CH₂Cl₂, -10 deg C, 1.5 h, -10 deg C --> room temp., 1.5 h

2: 82 percent / hydrogen / 10percent Pd/C poisoned with quinoline-sulfur / methanol; H₂O / 0.58 h

With hydrogen; dicyclohexyl-carbodiimide; Pd/C poisoned with quinoline-sulfur; In methanol; water;

DOI:10.1002/hlca.19870700505

Reference yield:

4-Hydrazinobenzoic acid (619-67-0) → β-N-[γ-L-(+)glutamyl]-4-(hydroxymethyl)phenylhydrazine (2757-90-6)

Guidance literature:

Multi-step reaction with 3 steps

1: (i) Et₃N, ClCO₂Et, (ii) /BRN= 387378/, Et₃N

2: BH₃ / tetrahydrofuran

3: H₂ / Pd-C

With borane; hydrogen; palladium on activated charcoal; In tetrahydrofuran;

DOI:10.1021/jo01336a003

upstream raw materials:

N²-(benzyloxycarbonyl)-L-glutamic acid 1-(benzyl ester) 5-(2-<4-(hydroxymethyl)phenyl>hydrazide)

Cbz-(L)-Glu-OBn

(p-hydroxymethylphenyl)hydrazine

methyl 4-hydrazinobenzoate

Refernces

• 1、 Kelly et al.. "-". . p. 3229. Retrieved 1962.