3'-O,4'-N-carbonyl-3'-O-desmethyl-4'-N-desmethyl-6-N,4'-N-bis<(benzyloxy)methyl>-ent-1'-iodo-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-1'-iodo-7-oxostaurosporine
• CAS No.: 174291-00-0
• Molecular Formula: C₄₃H₃₃IN₄O₇
• Molecular Weight: 844.662
• Mol file: 174291-00-0.mol

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

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

There total 8 articles about 3'-O,4'-N-carbonyl-3'-O-desmethyl-4'-N-desmethyl-6-N,4'-N-bis<(benzyloxy)methyl>-ent-1'-iodo-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: 65.0%

1-<(benzyloxy)methyl>-12-(3-<<(benzyloxy)methyl>amino>-3-N,4-O-carbonyl-2,6-dideoxy-5,6-anhydro-α-D-allopyranosyl)indolo<2.3-a>pyrrolo<3,4-c>carbazole-5,7-dione (174290-99-4) → 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)

Guidance literature:

With potassium tert-butylate; iodine; In tetrahydrofuran; methanol; for 3h; Ambient temperature;

DOI:10.1021/ja952907g

Reference yield:

1-<(benzyloxy)methyl>-3,4-dihydro-4-(<3-<<(benzyloxy)methyl>amino>-3-N,4-O-carbonyl-6-O-(4-methoxybenzyl)-2-deoxy-α-D-allopyranosyl>-1H-indol-3-yl)-3-(1-<2-(trimethylsilyl)ethoxymethyl>-1H-indol-3-yl)-1H-pyrrole-2,5-dione (174290-94-9) → 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)

Guidance literature:

Multi-step reaction with 6 steps

1: 97 percent / DDQ, H₂O / CH₂Cl₂ / Ambient temperature

2: 91 percent / tetrabutylammonium fluoride, molecular sieves 4A / tetrahydrofuran / 2.5 h / Heating

3: 73 percent / I₂, air / benzene / 8 h / Ambient temperature; Irradiation

4: 84 percent / I₂, Ph₃P, imidazole / CH₂Cl₂ / 6 h / Ambient temperature

5: 89 percent / DBU / tetrahydrofuran / 0.17 h / 0 °C

6: 65 percent / KOt-Bu, I₂ / tetrahydrofuran; methanol / 3 h / Ambient temperature

With 1H-imidazole; air; 4 A molecular sieve; potassium tert-butylate; tetrabutyl ammonium fluoride; water; iodine; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; dichloromethane; benzene;

DOI:10.1021/ja952907g

Reference yield:

1-<(benzyloxy)methyl>-12-(3-<<(benzyloxy)methyl>amino>-3-N,4-O-carbonyl-2-deoxy-α-D-allopyranosyl)indolo<2.3-a>pyrrolo<3,4-c>carbazole-5,7-dione (174290-97-2) → 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)

Guidance literature:

Multi-step reaction with 3 steps

1: 84 percent / I₂, Ph₃P, imidazole / CH₂Cl₂ / 6 h / Ambient temperature

2: 89 percent / DBU / tetrahydrofuran / 0.17 h / 0 °C

3: 65 percent / KOt-Bu, I₂ / tetrahydrofuran; methanol / 3 h / Ambient temperature

With 1H-imidazole; potassium tert-butylate; iodine; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/ja952907g

upstream raw materials:

1-<(benzyloxy)methyl>-12-(3-<<(benzyloxy)methyl>amino>-3-N,4-O-carbonyl-2,6-dideoxy-5,6-anhydro-α-D-allopyranosyl)indolo<2.3-a>pyrrolo<3,4-c>carbazole-5,7-dione

1-<(benzyloxy)methyl>-3,4-dihydro-4-(<3-<<(benzyloxy)methyl>amino>-3-N,4-O-carbonyl-2-deoxy-α-D-allopyranosyl>-1H-indol-3-yl)-3-(1H-indol-3-yl)-1H-pyrrole-2,5-dione

1-<(benzyloxy)methyl>-12-(3-<<(benzyloxy)methyl>amino>-3-N,4-O-carbonyl-2-deoxy-α-D-allopyranosyl)indolo<2.3-a>pyrrolo<3,4-c>carbazole-5,7-dione

1-<(benzyloxy)methyl>-12-(3-<<(benzyloxy)methyl>amino>-3-N,4-O-carbonyl-2,6-dideoxy-6-iodo-α-D-allopyranosyl)indolo<2.3-a>pyrrolo<3,4-c>carbazole-5,7-dione

Downstream raw materials:

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