Amicetin

Base Information

• Chemical Name: Amicetin
• CAS No.: 17650-86-1
• Molecular Formula: C29H42 N6 O9
• Molecular Weight: 618.687
• UNII: 0909X15C85
• DSSTox Substance ID: DTXSID801015583
• Nikkaji Number: J14.617J
• Wikidata: Q27236433
• Metabolomics Workbench ID: 116799
• Mol file: 17650-86-1.mol

Synonyms:amicetin

Chemical Property of Amicetin

Chemical Property:

• Melting Point: 244-245°
• Refractive Index: 1.6400 (estimate)
• Boiling Point: 660.6°C (rough estimate)
• PKA: pKa = 10.4, 7.0(at 25℃)
• PSA: 210.73000
• Density: 1.46g/cm³
• LogP: 0.46960
• XLogP3: -1
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 9
• Exact Mass: 618.30132694
• Heavy Atom Count: 44
• Complexity: 1110

Purity/Quality:

99% ^*data from raw suppliers

AMICETIN-A 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(CCC(O1)N2C=CC(=NC2=O)NC(=O)C3=CC=C(C=C3)NC(=O)C(C)(CO)N)OC4C(C(C(C(O4)C)N(C)C)O)O
• Isomeric SMILES: C[C@@H]1[C@H](CC[C@@H](O1)N2C=CC(=NC2=O)NC(=O)C3=CC=C(C=C3)NC(=O)[C@](C)(CO)N)O[C@@H]4[C@@H]([C@H]([C@@H]([C@H](O4)C)N(C)C)O)O

Technology Process of Amicetin

There total 11 articles about Amicetin 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:

amicetin → amicetin (17650-86-1)

Guidance literature:

With trifluoroacetic acid; In 1,2-dichloro-ethane; at 0 - 20 ℃; for 0.5h; Inert atmosphere;

DOI:10.1002/cjoc.202100284

Reference yield:

C22H32N2O6 → amicetin (17650-86-1)

Guidance literature:

Multi-step reaction with 6 steps

1: lithium hydroxide monohydrate / tetrahydrofuran; water / 50 °C / Inert atmosphere

2: hydrogenchloride / water / 80 °C / Inert atmosphere

3: 1H-imidazole / N,N-dimethyl-formamide / 12 h / 20 °C / Inert atmosphere

4: HATU; N-ethyl-N,N-diisopropylamine / 1,2-dichloro-ethane / 0.5 h / 70 °C / Microwave irradiation; Inert atmosphere

5: triethylamine hydrofluoride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

6: trifluoroacetic acid / 1,2-dichloro-ethane / 0.5 h / 0 - 20 °C / Inert atmosphere

With 1H-imidazole; hydrogenchloride; lithium hydroxide monohydrate; triethylamine hydrofluoride; N-ethyl-N,N-diisopropylamine; HATU; trifluoroacetic acid; In tetrahydrofuran; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1002/cjoc.202100284

Reference yield:

(S)-methyl 4-(2-amino-2-methyl-3-(tert-butyldimethylsilyloxy)-propanamido)benzoate → amicetin (17650-86-1)

Guidance literature:

Multi-step reaction with 3 steps

1: HATU; N-ethyl-N,N-diisopropylamine / 1,2-dichloro-ethane / 0.5 h / 70 °C / Microwave irradiation; Inert atmosphere

2: triethylamine hydrofluoride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

3: trifluoroacetic acid / 1,2-dichloro-ethane / 0.5 h / 0 - 20 °C / Inert atmosphere

With triethylamine hydrofluoride; N-ethyl-N,N-diisopropylamine; HATU; trifluoroacetic acid; In tetrahydrofuran; 1,2-dichloro-ethane;

DOI:10.1002/cjoc.202100284

upstream raw materials:

4-methoxycarbonyl aniline

Downstream raw materials:

Cytosine

bamicetin

Refernces

• 1、 Chen, Ruidong,Zhang, Haibo,Zhang, Gaiyun,Li, Sumei,Zhang, Guangtao,Zhu, Yiguang,Liu, Jinsong,Zhang, Changsheng. "Characterizing amosamine biosynthesis in amicetin reveals amig as a reversible retaining glycosyltransferase". supporting information. p. 12152 - 12155. Retrieved 2013/09/23.