3'-O,4'-N-carbonyl-3'-O-desmethyl-4'-N-desmethyl-6-N,4'-N-bis<(benzyloxy)methyl>-ent-7-oxostaurosporine

Base Information

• Chemical Name: 3'-O,4'-N-carbonyl-3'-O-desmethyl-4'-N-desmethyl-6-N,4'-N-bis<(benzyloxy)methyl>-ent-7-oxostaurosporine
• CAS No.: 174291-02-2
• Molecular Formula: C₄₃H₃₄N₄O₇
• Molecular Weight: 718.766
• Mol file: 174291-02-2.mol

Synonyms:3'-O,4'-N-carbonyl-3'-O-desmethyl-4'-N-desmethyl-6-N,4'-N-bis<(benzyloxy)methyl>-ent-7-oxostaurosporine

Chemical Property of 3'-O,4'-N-carbonyl-3'-O-desmethyl-4'-N-desmethyl-6-N,4'-N-bis<(benzyloxy)methyl>-ent-7-oxostaurosporine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3'-O,4'-N-carbonyl-3'-O-desmethyl-4'-N-desmethyl-6-N,4'-N-bis<(benzyloxy)methyl>-ent-7-oxostaurosporine

There total 1 articles about 3'-O,4'-N-carbonyl-3'-O-desmethyl-4'-N-desmethyl-6-N,4'-N-bis<(benzyloxy)methyl>-ent-7-oxostaurosporine 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: 99.0%

3'-O,4'-N-carbonyl-3'-O-desmethyl-4'-N-desmethyl-6-N,4'-N-bis<(benzyloxy)methyl>-ent-1'-iodo-7-oxostaurosporine (174291-00-0) → 3'-O,4'-N-carbonyl-3'-O-desmethyl-4'-N-desmethyl-6-N,4'-N-bis<(benzyloxy)methyl>-ent-7-oxostaurosporine (174291-02-2)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In benzene; for 0.5h; Heating;

DOI:10.1021/ja952907g

Reference yield:

3'-O,4'-N-carbonyl-3'-O-desmethyl-4'-N-desmethyl-6-N,4'-N-bis<(benzyloxy)methyl>-ent-7-oxostaurosporine (174291-02-2) → staurosporine (62996-74-1)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) H₂, Pd(OH)2/C, 2.) NaOMe / 1.) AcOEt, MeOH, RT, overnight, 2.) MeOH, 30 min

2: 81 percent / DMAP, Et₃N / tetrahydrofuran / Ambient temperature

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

4: 93 percent / Cs₂CO₃ / methanol / 0.75 h / Ambient temperature

5: 86 percent / NaH / tetrahydrofuran; dimethylformamide / 2 h / Ambient temperature

6: 1.) H₂, Pd(OH)2/C, 2.) NaOMe / 1.) EtOAc, MeOH, RT, overnight, 2.) MeOH, RT, 30 min

7: 97 percent / TFA / CH₂Cl₂ / 0.25 h / Ambient temperature

8: 1.) NaBH₄, 2.) PhSeH, TsOH*H₂O / 1.) EtOH, RT, 4 h, 2.) CH₂Cl₂, RT, 1 h

With dmap; palladium dihydroxide; sodium tetrahydroborate; hydrogen; sodium methylate; Benzeneselenol; sodium hydride; caesium carbonate; toluene-4-sulfonic acid; triethylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja952907g

Reference yield:

3'-O,4'-N-carbonyl-3'-O-desmethyl-4'-N-desmethyl-6-N,4'-N-bis<(benzyloxy)methyl>-ent-7-oxostaurosporine (174291-02-2) → 6-N-<(benzyloxy)methyl>-3'-O,4'-N-carbonyl-3'-O-desmethyl-4'-N-desmethyl-ent-7-oxo-4'-N-(tert-butyloxycarbonyl)staurosporine (174291-05-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) H₂, Pd(OH)2/C, 2.) NaOMe / 1.) AcOEt, MeOH, RT, overnight, 2.) MeOH, 30 min

2: 81 percent / DMAP, Et₃N / tetrahydrofuran / Ambient temperature

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

With dmap; palladium dihydroxide; hydrogen; sodium methylate; sodium hydride; triethylamine; In tetrahydrofuran;

DOI:10.1021/ja952907g

upstream raw materials:

3'-O,4'-N-carbonyl-3'-O-desmethyl-4'-N-desmethyl-6-N,4'-N-bis<(benzyloxy)methyl>-ent-1'-iodo-7-oxostaurosporine

Downstream raw materials:

staurosporine

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

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

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