Rachelmycin

Base Information

• Chemical Name: Rachelmycin
• CAS No.: 69866-21-3
• Molecular Formula: C37H33 N7 O8
• Molecular Weight: 703.711
• DSSTox Substance ID: DTXSID40990138
• Wikidata: Q108730872
• ChEMBL ID: CHEMBL139109
• Mol file: 69866-21-3.mol

Synonyms:Benzo(1,2-b:4,3-b')dipyrrole-3(2H)-carboxamide, 7-((1,6-dihydro-4-hydroxy-5-methoxy-7-((4,5,8,8a-tetrahydro-7-methyl-4-oxocyclopropa(c)pyrrolo(3,2-e)indol-2(1H)-yl)carbonyl)benzo(1,2-b:4,3-b')dipyrrol-3(2H)-yl)carbonyl)-1,6-dihydro-4-hydroxy-5-methox;CC 1065;CC-1065;NSC 298223

Chemical Property of Rachelmycin

Chemical Property:

• Refractive Index: 1.6910 (estimate)
• Boiling Point: 704.36°C (rough estimate)
• PSA: 210.31000
• Density: 1.75g/cm³
• LogP: 4.62030
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 4
• Exact Mass: 703.23906104
• Heavy Atom Count: 52
• Complexity: 1610

Purity/Quality:

99% ^*data from raw suppliers

RACHELMYCIN 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CNC2=C1C34CC3CN(C4=CC2=O)C(=O)C5=CC6=C7CCN(C7=C(C(=C6N5)OC)O)C(=O)C8=CC9=C1CCN(C1=C(C(=C9N8)OC)O)C(=O)N
• Isomeric SMILES: CC1=CNC2=C1[C@@]34C[C@@H]3CN(C4=CC2=O)C(=O)C5=CC6=C7CCN(C7=C(C(=C6N5)OC)O)C(=O)C8=CC9=C1CCN(C1=C(C(=C9N8)OC)O)C(=O)N

Technology Process of Rachelmycin

There total 52 articles about Rachelmycin 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: 45.0%

C37H34ClN7O8 (112764-71-3) → CC-1065 (69866-21-3)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; for 4h; Ambient temperature;

DOI:10.3987/COM-97-7920

Reference yield:

(S)-1,6-dihydro-1-(hydroxymethyl)-8-methyl-5-(phenylmethoxy)-benzo[1,2-b:4,3-b']dipyrrole-3(2H)-carboxylic acid 1,1-dimethylethyl ester (112836-67-6) → CC-1065 (69866-21-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 82 percent / PPh₃, CCl₄ / CH₂Cl₂ / 7 h / Ambient temperature

2: 88 percent / 25percent HCO₂NH₄ / 10percentPd-C / tetrahydrofuran / 6 h / 0 °C

3: 3M HCl / ethyl acetate / 1 h / Ambient temperature

4: 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / dimethylformamide / Ambient temperature

5: 45 percent / DBU / acetonitrile / 4 h / Ambient temperature

With hydrogenchloride; tetrachloromethane; ammonium formate; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triphenylphosphine; 10% palladium on active carbon; In tetrahydrofuran; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;

DOI:10.3987/COM-97-7920

Reference yield:

(S)-1-(chloromethyl)-1,6-dihydro-8-methyl-5-(phenylmethoxy)-benzo[1,2-b:4,3-b']dipyrrole-3(2H)-carboxylic acid 1,1-dimethylethyl ester (110314-50-6) → CC-1065 (69866-21-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 88 percent / 25percent HCO₂NH₄ / 10percentPd-C / tetrahydrofuran / 6 h / 0 °C

2: 3M HCl / ethyl acetate / 1 h / Ambient temperature

3: 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / dimethylformamide / Ambient temperature

4: 45 percent / DBU / acetonitrile / 4 h / Ambient temperature

With hydrogenchloride; ammonium formate; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 10% palladium on active carbon; In tetrahydrofuran; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;

DOI:10.3987/COM-97-7920

upstream raw materials:

C₃₇H₃₄ClN₇O₈

tert-butyl-(1S)-1-(chloromethyl)-5-hydroxy-8-methyl-1,6-dihydropyrrolo[3,2-e]indole-3(2H)-carboxylate

(S)-1,6-dihydro-1-(hydroxymethyl)-8-methyl-5-(phenylmethoxy)-benzo[1,2-b:4,3-b']dipyrrole-3(2H)-carboxylic acid 1,1-dimethylethyl ester

(S)-1-(chloromethyl)-1,6-dihydro-8-methyl-5-(phenylmethoxy)-benzo[1,2-b:4,3-b']dipyrrole-3(2H)-carboxylic acid 1,1-dimethylethyl ester

Refernces

Total synthesis of PDE-II by copper-mediated double amination

10.1039/b926965g

The research presents a concise total synthesis of PDE-II, a compound with inhibitory activity towards cyclic adenosine-3',5'-monophosphate phosphodiesterase, using a copper-mediated double aryl amination method. The purpose of this study is to develop an efficient and straightforward route for synthesizing PDE-II, given its importance as a partial structure of potent DNA alkylating agents like CC-1065 and yatakemycin. The synthesis involves a one-pot five-step sequence, starting from tetrahydroisoquinoline 7, and includes steps such as transacetalization, introduction of a glycine moiety, double aryl amination, and selective reduction. The study concludes that the developed method allows for the synthesis of PDE-II in 7.5% yield over 11 steps, demonstrating a significant improvement in efficiency compared to previous methods. The findings suggest that this synthetic strategy could be generally applicable to a wide variety of nitrogen-containing heterocycles due to the high utility of the aryl amination reaction.

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