5'-Deoxytoyocamycin

Base Information

• Chemical Name: 5'-Deoxytoyocamycin
• CAS No.: 65562-55-2
• Molecular Formula: C12H13N5O3
• Molecular Weight: 275.2633
• DSSTox Substance ID: DTXSID60984150
• Nikkaji Number: J399.009E
• Wikidata: Q82971268
• ChEMBL ID: CHEMBL99388
• Mol file: 65562-55-2.mol

Synonyms:5'-deoxytoyocamycin

Chemical Property of 5'-Deoxytoyocamycin

Chemical Property:

• Vapor Pressure: 1.75E-17mmHg at 25°C
• Boiling Point: 644.3°Cat760mmHg
• Flash Point: 343.5°C
• PSA: 26.02000
• Density: 1.78g/cm³
• LogP: 3.58990
• XLogP3: -1.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 1
• Exact Mass: 275.10183929
• Heavy Atom Count: 20
• Complexity: 427

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(C(C(O1)N2C=C(C3=C(N=CN=C32)N)C#N)O)O
• Isomeric SMILES: C[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=C(C3=C(N=CN=C32)N)C#N)O)O

Technology Process of 5'-Deoxytoyocamycin

There total 14 articles about 5'-Deoxytoyocamycin 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: 81.0%

4-amino-5-cyano-7-(5-chloro-5-deoxy-β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine (65562-54-1) → 5'-deoxytoyocamycin (65562-55-2)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In tetrahydrofuran; for 18h; Heating;

DOI:10.1021/jm990205m

Reference yield: 67.0%

N4-benzoyl-5-cyano-7-(2',3'-di-O-acetyl-5'-deoxy-β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine → 5'-deoxysangivamycin (65562-56-3) + 5'-deoxytoyocamycin (65562-55-2)

Guidance literature:

With ammonium hydroxide; In 1,4-dioxane; at 45 ℃; for 21h;

DOI:10.3390/molecules24040737

Reference yield:

2-bromo-5-(ethoxymethyleneamino)pyrrole-3,4-dicarbonitrile (110089-43-5) → 5'-deoxysangivamycin (65562-56-3) + 5'-deoxytoyocamycin (65562-55-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: ammonia / ethanol / 5 h / 105 °C

2.1: triethylamine / acetonitrile / 1 h / 20 °C

3.1: ammonium hydroxide / water / 5 h

4.1: N,O-bis-(trimethylsilyl)-acetamide / acetonitrile / 1 h / 20 °C / Inert atmosphere

4.2: Inert atmosphere; Cooling with ice

5.1: triethylamine; palladium 10% on activated carbon; hydrogen / tetrahydrofuran; methanol / 2.25 h / 20 °C / 760.05 Torr

6.1: ammonium hydroxide / 1,4-dioxane / 21 h / 45 °C

With ammonium hydroxide; N,O-bis-(trimethylsilyl)-acetamide; palladium 10% on activated carbon; ammonia; hydrogen; triethylamine; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; water; acetonitrile; 4.2: |Vorbrueggen Nucleoside Synthesis;

DOI:10.3390/molecules24040737

upstream raw materials:

4-amino-5-cyano-7-(5-chloro-5-deoxy-β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine

4-amino-5-cyano-7-(5-deoxy-2,3-di-O-acetyl-β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine

5-deoxy-1,2,3-tri-O-acetyl-D-ribofuranose

4-amino-6-bromo-5-cyanopyrrolo[2,3-d]pyrimidine