Iejimalide B

Base Information

• Chemical Name: Iejimalide B
• CAS No.: 117582-92-0
• Molecular Formula: C41H60 N2 O7
• Molecular Weight: 692.9243
• UNII: 7AT5FEX4Z8
• Nikkaji Number: J891.411G
• Wikidata: Q27147352
• Metabolomics Workbench ID: 180576
• Mol file: 117582-92-0.mol

Synonyms:iejimalide B

Chemical Property of Iejimalide B

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 882.7°Cat760mmHg
• Flash Point: 487.6°C
• PSA: 123.19000
• Density: 1.08g/cm³
• LogP: 7.98140
• XLogP3: 7.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 9
• Exact Mass: 692.44005226
• Heavy Atom Count: 50
• Complexity: 1360

Purity/Quality:

≥98% （HPLC） ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C=CC(=CC(CC=CC(=CCCC(C=CC=CC(C(OC(=O)C(=C1)C)C(=CC=C(C)CNC(=O)C(CO)NC=O)C)C)OC)C)OC)C
• Isomeric SMILES: C[C@@H]\1/C=C/C(=C/[C@H](C/C=C/C(=C\CC[C@@H](/C=C/C=C/[C@@H]([C@H](OC(=O)/C(=C1)/C)/C(=C/C=C(\C)/CNC(=O)[C@H](CO)NC=O)/C)C)OC)/C)OC)/C

Technology Process of Iejimalide B

There total 63 articles about Iejimalide B 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-(tert-butyl-dimethyl-silanyloxy)-N-[5-(8,16-dimethoxy-3,12,18,21,23-pentamethyl-24-oxo-oxacyclotetracosa-4,6,11,13,17,19,22-heptaen-2-yl)-2-methyl-hexa-2,4-dienyl]-2-formylamino-propionamide (914300-91-7) → iejimalide B (117582-92-0)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 0.25h; Inert atmosphere;

DOI:10.1002/chem.201100178

Reference yield:

(2E,4R,5E,7E,9S)-9-methoxy-2,4,7-trimethyldodeca-2,5,7,11-tetraenoic acid (914300-79-1) → iejimalide B (117582-92-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: DCC; 4-pyrrolidinyl-pyridine / CH₂Cl₂ / 0.17 h / 0 °C

1.2: 85 percent / CH₂Cl₂ / 17 h / 0 - 20 °C

2.1: 69 percent / Grubbs second generation catalyst / CH₂Cl₂ / 48 h / 20 °C

3.1: 80 percent / TBAF / tetrahydrofuran / 0.25 h / 0 °C

With tetrabutyl ammonium fluoride; dicyclohexyl-carbodiimide; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; dichloromethane; 1.2: Yonemitsu reaction;

DOI:10.1021/ja072334v

Reference yield:

(S)-3-(tert-butyldimethylsilyloxy)-2-formamido-N-((2E,4E,6S,7S,8E)-6-hydroxy-9-iodo-2,5,7-trimethylnona-2,4,8-trienyl)propanamide (914300-88-2) → iejimalide B (117582-92-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 70 percent / Ba(OH)2*8H₂O / Pd(dppf)Cl₂ / dimethylformamide / 3 h / 20 °C

2.1: DCC; 4-pyrrolidinyl-pyridine / CH₂Cl₂ / 0.17 h / 0 °C

2.2: 85 percent / CH₂Cl₂ / 17 h / 0 - 20 °C

3.1: 69 percent / Grubbs second generation catalyst / CH₂Cl₂ / 48 h / 20 °C

4.1: 80 percent / TBAF / tetrahydrofuran / 0.25 h / 0 °C

With barium dihydroxide; tetrabutyl ammonium fluoride; dicyclohexyl-carbodiimide; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 1.1: Suzuki reaction / 2.2: Yonemitsu reaction;

DOI:10.1021/ja072334v

upstream raw materials:

3-(tert-butyl-dimethyl-silanyloxy)-N-[5-(8,16-dimethoxy-3,12,18,21,23-pentamethyl-24-oxo-oxacyclotetracosa-4,6,11,13,17,19,22-heptaen-2-yl)-2-methyl-hexa-2,4-dienyl]-2-formylamino-propionamide

(6Z,3S)-3-methoxy-7-methylnona-6,8-dien-1-yne

(4S)-4-methoxy-6-(trimethylsilyl)hex-5-ynal

(3S)-1-(trimethylsilyl)hept-6-en-1-yn-3-ol

Refernces

• 1、 Gagnepain, Julien,Moulin, Emilie,Fuerstner, Alois. "Gram-scale synthesis of iejimalide B". supporting information; experimental part. p. 6964 - 6972. Retrieved 2011/07/30.
• 2、 Fuerstner, Alois,Nevado, Cristina,Waser, Mario,Tremblay, Martin,Chevrier, Carine,Teply, Filip,Aissa, Christophe,Moulin, Emilie,Mueller, Oliver. "Total synthesis of iejimalide A-D and assessment of the remarkable actin-depolymerizing capacity of these polyene macrolides". . p. 9150 - 9161. Retrieved 2008/02/10.