6-N-<(benzyloxy)methyl>-ent-7-oxo-4'-N-(tert-butyloxycarbonyl)staurosporine

Base Information

• Chemical Name: 6-N-<(benzyloxy)methyl>-ent-7-oxo-4'-N-(tert-butyloxycarbonyl)staurosporine
• CAS No.: 174148-74-4
• Molecular Formula: C₄₁H₄₀N₄O₇
• Molecular Weight: 700.791
• Mol file: 174148-74-4.mol

Synonyms:6-N-<(benzyloxy)methyl>-ent-7-oxo-4'-N-(tert-butyloxycarbonyl)staurosporine

Chemical Property of 6-N-<(benzyloxy)methyl>-ent-7-oxo-4'-N-(tert-butyloxycarbonyl)staurosporine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-N-<(benzyloxy)methyl>-ent-7-oxo-4'-N-(tert-butyloxycarbonyl)staurosporine

There total 7 articles about 6-N-<(benzyloxy)methyl>-ent-7-oxo-4'-N-(tert-butyloxycarbonyl)staurosporine 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: 86.0%

dimethyl sulfate (77-78-1) + 6-N-<(benzyloxy)methyl>-3'-O-desmethyl-4'-N-desmethyl-ent-7-oxo-4'-N-(tert-butyloxycarbonyl)staurosporine (174291-06-6) → 6-N-<(benzyloxy)methyl>-ent-7-oxo-4'-N-(tert-butyloxycarbonyl)staurosporine (174148-74-4)

Guidance literature:

With sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; for 2h; Ambient temperature;

DOI:10.1021/ja952907g

Reference yield:

Benzyloxymethyl chloride (3587-60-8) → 6-N-<(benzyloxy)methyl>-ent-7-oxo-4'-N-(tert-butyloxycarbonyl)staurosporine (174148-74-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) NaH / 1.) DMF, RT, 15 min, 2.) DMF, RT, 30 min

2: 93 percent / Cs₂CO₃ / methanol / 0.75 h / Ambient temperature

3: 86 percent / NaH / tetrahydrofuran; dimethylformamide / 2 h / Ambient temperature

With sodium hydride; caesium carbonate; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1021/ja952907g

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → 6-N-<(benzyloxy)methyl>-ent-7-oxo-4'-N-(tert-butyloxycarbonyl)staurosporine (174148-74-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 81 percent / DMAP, Et₃N / tetrahydrofuran / Ambient temperature

2: 1.) NaH / 1.) DMF, RT, 15 min, 2.) DMF, RT, 30 min

3: 93 percent / Cs₂CO₃ / methanol / 0.75 h / Ambient temperature

4: 86 percent / NaH / tetrahydrofuran; dimethylformamide / 2 h / Ambient temperature

With dmap; sodium hydride; caesium carbonate; triethylamine; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1021/ja952907g

upstream raw materials:

dimethyl sulfate

6-N-<(benzyloxy)methyl>-3'-O-desmethyl-4'-N-desmethyl-ent-7-oxo-4'-N-(tert-butyloxycarbonyl)staurosporine

Benzyloxymethyl chloride

di-tert-butyl dicarbonate

Downstream raw materials:

staurosporine

ent-7-oxostaurosporine

Refernces

• 1、 Link,Raghavan, Subharekha,Danishefsky, Samuel J.. "First total synthesis of staurosporine and ent-staurosporine". . p. 552 - 553. Retrieved 2007/10/02.