4'-Demethylamino-4',5'-dihydroxystaurosporine

Base Information

• Chemical Name: 4'-Demethylamino-4',5'-dihydroxystaurosporine
• CAS No.: 155416-34-5
• Molecular Formula: C27H23 N3 O5
• Molecular Weight: 469.49
• Nikkaji Number: J576.179D
• ChEMBL ID: CHEMBL4762704
• Mol file: 155416-34-5.mol

Synonyms:4'-demethylamino-4',5'-dihydroxy-staurosporine;4'-demethylamino-4',5'-dihydroxystaurosporine;MLR 52;MLR-52

Chemical Property of 4'-Demethylamino-4',5'-dihydroxystaurosporine

Chemical Property:

• Boiling Point: 732.6°Cat760mmHg
• PKA: 13.21±0.70(Predicted)
• Flash Point: 396.9°C
• PSA: 97.88000
• Density: 1.71g/cm³
• LogP: 3.42650
• XLogP3: 2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 469.16377084
• Heavy Atom Count: 35
• Complexity: 919

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

Technology Process of 4'-Demethylamino-4',5'-dihydroxystaurosporine

There total 13 articles about 4'-Demethylamino-4',5'-dihydroxystaurosporine 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: 77.0%

C36H33N3O7 (188028-00-4) → staurosporine (155416-34-5)

Guidance literature:

With methoxybenzene; trifluoroacetic acid;

DOI:10.1021/ja9626143

Reference yield: 65.0%

C27H21N3O3 (169756-23-4) → staurosporine (155416-34-5)

Guidance literature:

With osmium(VIII) oxide; 4-methylmorpholine N-oxide;

DOI:10.7164/antibiotics.53.426

Reference yield:

C36H31N3O7 (188028-91-3) → staurosporine (155416-34-5)

Guidance literature:

Multi-step reaction with 8 steps

1: 89 percent / LiBH₄ / tetrahydrofuran / 0.33 h

2: 71 percent / pyridinium trifluoroacetate, 1,3-dicyclohexylcarbodiimide / benzene; dimethylsulfoxide / 9 h / Ambient temperature

3: 85 percent / BF₃*OEt₂ / diethyl ether / 24 h / 25 - 30 °C

4: 95 percent / NaBH₄ / methanol; CH₂Cl₂; CHCl₃ / 0.08 h

5: 1.) NaH / 1) THF, 25 min; 2) THF, 50 min

6: 88 percent / Martin's sulfurane / CDCl₃ / 0.33 h

7: 84 percent / 4-methylmorpholine-N-oxide, OsO₄ / 2-methyl-propan-2-ol; acetone; H₂O / 16 h

8: 77 percent / TFA, anisole / 16 h

With sodium tetrahydroborate; osmium(VIII) oxide; lithium borohydride; Martins sulfurane; boron trifluoride diethyl etherate; pyridinium trifluroacetate; sodium hydride; methoxybenzene; 4-methylmorpholine N-oxide; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; methanol; diethyl ether; chloroform-d1; dichloromethane; chloroform; water; dimethyl sulfoxide; acetone; tert-butyl alcohol; benzene;

DOI:10.1021/ja971304x

upstream raw materials:

C₃₆H₃₃N₃O₇

C₂₇H₂₁N₃O₃

staurosporine

(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

Downstream raw materials:

(+)-RK-286c

C₂₇H₂₃N₃O₄

Refernces

• 1、 Wood, John L.,Stoltz, Brian M.,Goodman, Steven N.,Onwueme, Kenolisa. "Design and implementation of an efficient synthetic approach to pyranosylated indolocarbazoles: Total synthesis of (+)-RK286c, (+)-MLR-52, (+)-staurosporine, and (-)-TAN-1030a". . p. 9652 - 9661. Retrieved 2007/10/03.