N,N-Dimethylstaurosporine

Base Information

• Chemical Name: N,N-Dimethylstaurosporine
• CAS No.: 129623-30-9
• Molecular Formula: C29H28 N4 O3
• Molecular Weight: 480.5576
• Nikkaji Number: J768.916K
• Wikidata: Q105180124
• Metabolomics Workbench ID: 101935
• Mol file: 129623-30-9.mol

Synonyms:N,N-dimethyl-staurosporine;N,N-dimethylstaurosporine

Chemical Property of N,N-Dimethylstaurosporine

Chemical Property:

• Vapor Pressure: 5.55E-18mmHg at 25°C
• Boiling Point: 673.2°Cat760mmHg
• Flash Point: 360.9°C
• PSA: 60.66000
• Density: 1.5g/cm³
• LogP: 5.02500
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 480.21614077
• Heavy Atom Count: 36
• Complexity: 930

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC12C(C(CC(O1)N3C4=CC=CC=C4C5=C6C(=C7C8=CC=CC=C8N2C7=C53)CNC6=O)N(C)C)OC
• Isomeric SMILES: C[C@@]12[C@@H]([C@@H](C[C@@H](O1)N3C4=CC=CC=C4C5=C6C(=C7C8=CC=CC=C8N2C7=C53)CNC6=O)N(C)C)OC

Technology Process of N,N-Dimethylstaurosporine

There total 1 articles about N,N-Dimethylstaurosporine 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: 100.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + staurosporine (62996-74-1) → (5S,6R,7R,9R)-6-methoxy-5-methyl-7-(methylamino)-6,7,8,9,15,16-hexahydro-17-oxa-4b,9a,15-triaza-5,9-methanodibenzo[b,h]cyclonona[jkl]cyclopenta[e]-as-indacen-14(5h)-one (129623-30-9)

Guidance literature:

With sodium cyanoborohydride;

DOI:10.7164/antibiotics.53.426

Reference yield:

(5S,6R,7R,9R)-6-methoxy-5-methyl-7-(methylamino)-6,7,8,9,15,16-hexahydro-17-oxa-4b,9a,15-triaza-5,9-methanodibenzo[b,h]cyclonona[jkl]cyclopenta[e]-as-indacen-14(5h)-one (129623-30-9) → (+)-RK-286c (126572-73-4,145212-39-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 92 percent / m-chloroperoxybenzoic acid (m-CPBA) / CHCl₃

2: 85 percent / 160 °C / 1 Torr

3: 65 percent / OsO₄; N-methylmorpholine-N-oxide (NMO)

4: 60 percent / tetrahydrofuran

5: 47 percent / n-Bu₃SnH; 2,2'-azobisisobutyronitrile (AIBN) / toluene

6: 80 percent

7: 50 percent / potassium tri-sec-butyl borohydride (K-Selectride)

With osmium(VIII) oxide; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; potassium tri-sec-butyl-borohydride; 4-methylmorpholine N-oxide; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; chloroform; toluene; 1: Oxidation / 2: Elimination / 3: Oxidation / 4: Substitution / 5: Reduction / 6: Oxidation / 7: Reduction;

DOI:10.7164/antibiotics.53.426

Reference yield:

(5S,6R,7R,9R)-6-methoxy-5-methyl-7-(methylamino)-6,7,8,9,15,16-hexahydro-17-oxa-4b,9a,15-triaza-5,9-methanodibenzo[b,h]cyclonona[jkl]cyclopenta[e]-as-indacen-14(5h)-one (129623-30-9) → C27H23N3O4 (282103-07-5,145212-39-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 92 percent / m-chloroperoxybenzoic acid (m-CPBA) / CHCl₃

2: 85 percent / 160 °C / 1 Torr

3: 65 percent / OsO₄; N-methylmorpholine-N-oxide (NMO)

4: 60 percent / tetrahydrofuran

5: 47 percent / n-Bu₃SnH; 2,2'-azobisisobutyronitrile (AIBN) / toluene

With osmium(VIII) oxide; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; 4-methylmorpholine N-oxide; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; chloroform; toluene; 1: Oxidation / 2: Elimination / 3: Oxidation / 4: Substitution / 5: Reduction;

DOI:10.7164/antibiotics.53.426

upstream raw materials:

formaldehyd

staurosporine

Downstream raw materials:

(+)-RK-286c

staurosporine

C₂₇H₂₃N₃O₄