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

• 1、 Fukuda, Yasumichi,Furuta, Hirosuke,Shiga, Futoshi,Asahina, Yoshikazu,Terashima, Shiro. "Novel syntheses of optically active CC-1065, U-73,975(adozelesin), U-80,244(carzelesin), U-77,779(bizelesin), KW-2189, and DU-86". . p. 2303 - 2308. Retrieved 2007/10/03.
• 2、 Boger, Dale L.,Coleman, Robert S.. "Total Synthesis of (+)-CC-1065 and ent-(-)-CC-1065". . p. 1321 - 1323. Retrieved 2007/10/02.