Cyanomethyladriamycin

Base Information

• Chemical Name: Cyanomethyladriamycin
• CAS No.: 103450-92-6
• Molecular Formula: C₂₉H₃₀N₂O₁₁
• Molecular Weight: 582.564
• DSSTox Substance ID: DTXSID70908423
• Mol file: 103450-92-6.mol

Synonyms:Cyanomethyladriamycin;103450-92-6;N-(Cyanomethyl)doxorubicin;BRN 6038286;5,12-Naphthacenedione, 7,8,9,10-tetrahydro-10-((3-((cyanomethyl)amino)-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosyl)oxy)-8-(hydroxyacetyl)-1-methoxy-6,8,11-trihydroxy-, (8S-cis)-;DTXSID70908423;3,5,12-Trihydroxy-3-(hydroxyacetyl)-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-[(cyanomethyl)amino]-2,3,6-trideoxyhexopyranoside

Chemical Property of Cyanomethyladriamycin

Chemical Property:

• Vapor Pressure: 1.85E-33mmHg at 25°C
• Boiling Point: 883.6°C at 760 mmHg
• Flash Point: 488.2°C
• Density: 1.59g/cm³
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 13
• Rotatable Bond Count: 7
• Exact Mass: 582.18495978
• Heavy Atom Count: 42
• Complexity: 1110

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(C(CC(O1)OC2CC(CC3=C2C(=C4C(=C3O)C(=O)C5=C(C4=O)C(=CC=C5)OC)O)(C(=O)CO)O)NCC#N)O

Technology Process of Cyanomethyladriamycin

There total 3 articles about Cyanomethyladriamycin 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:

{(3aS,4S,6R,7aS)-4-Methyl-6-[(1S,3S)-3,5,12-trihydroxy-3-(1-hydroxy-1-hydroxymethyl-prop-2-ynyl)-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-1-yloxy]-tetrahydro-pyrano[4,3-d]oxazol-1-yl}-acetonitrile (103620-76-4) → N-(cyanomethyl)doxorubicin (103450-92-6) + N,N-bis(cyanomethyl)doxorubicin (103620-78-6)

Guidance literature:

With hydrogenchloride; In methanol; chloroform; at 23 ℃; for 17h; Yield given;

DOI:10.1021/jm00160a047

Reference yield:

doxorubicin hydrochloride (25316-40-9) → N-(cyanomethyl)doxorubicin (103450-92-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 0.5 N HCl / acetonitrile; H₂O; methanol / 1 h / 23 °C

2: 1.0 N HCl / CHCl₃; methanol / 17 h / 23 °C

With hydrogenchloride; In methanol; chloroform; water; acetonitrile;

DOI:10.1021/jm00160a047

Reference yield:

sodium cyanide (143-33-9,25596-52-5) + N-(1-cyano-2-methoxyethyl)doxorubicin (103450-90-4,103667-16-9,103667-17-0) → N-(cyanomethyl)doxorubicin (103450-92-6) + {(3aS,4S,6R,7aS)-4-Methyl-6-[(1S,3S)-3,5,12-trihydroxy-3-(2-hydroxy-acetyl)-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-1-yloxy]-tetrahydro-pyrano[4,3-d]oxazol-1-yl}-acetonitrile (103620-77-5)

Guidance literature:

In methanol; chloroform; acetone; at 23 ℃; for 16h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1021/jm00160a047

upstream raw materials:

sodium cyanide

N-(1-cyano-2-methoxyethyl)doxorubicin

{(3aS,4S,6R,7aS)-4-Methyl-6-[(1S,3S)-3,5,12-trihydroxy-3-(1-hydroxy-1-hydroxymethyl-prop-2-ynyl)-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-1-yloxy]-tetrahydro-pyrano[4,3-d]oxazol-1-yl}-acetonitrile

doxorubicin hydrochloride

Refernces