Fumitremorgin B

Base Information

• Chemical Name: Fumitremorgin B
• CAS No.: 12626-17-4
• Molecular Formula: C₂₇H₃₃N₃O₅
• Molecular Weight: 479.576
• UNII: ITN5B384F8
• DSSTox Substance ID: DTXSID70925478
• Nikkaji Number: J31.904J
• Wikidata: Q27133338
• Metabolomics Workbench ID: 63426
• ChEMBL ID: CHEMBL3885413
• Mol file: 12626-17-4.mol

Synonyms:fumitremorgin B

Chemical Property of Fumitremorgin B

Chemical Property:

• Vapor Pressure: 5.1E-22mmHg at 25°C
• Melting Point: 205-207 °C
• Boiling Point: 724.3°Cat760mmHg
• PKA: 10.74±0.60(Predicted)
• Flash Point: 391.8°C
• PSA: 95.24000
• Density: 1.35g/cm³
• LogP: 3.06800
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 479.24202116
• Heavy Atom Count: 35
• Complexity: 941

Purity/Quality:

99%, ^*data from raw suppliers

FUMITREMORGIN B 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCN1C2=C(C=CC(=C2)OC)C3=C1C(N4C(=O)C5CCCN5C(=O)C4(C3O)O)C=C(C)C)C
• Isomeric SMILES: CC(=CCN1C2=C(C=CC(=C2)OC)C3=C1[C@@H](N4C(=O)[C@@H]5CCCN5C(=O)[C@@]4([C@H]3O)O)C=C(C)C)C
• Description: This tremorgenic alkaloid is highly toxic and is elaborated by Aspergillus jurnigatus. The structure given above has been determined from X-ray crystallography. The crystals are orthorhombic with space group P2 1212 1, a = 14.771, b = 24.925 and c = 7.321 A with Z = 4. The absolute configuration is based upon that of L( - )-proline formed by acid hydrolysis of the alkaloid.

Technology Process of Fumitremorgin B

There total 23 articles about Fumitremorgin 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: 66.0%

12,13-Dihydroxyfumitremorgin C (111468-05-4,111468-06-5,111427-99-7) + 3,3-dimethyl-allyl chloride (503-60-6) → fumitremorgin B (111139-38-9,12626-17-4)

Guidance literature:

With potassium hydroxide; 18-crown-6 ether; In benzene;

DOI:10.1016/S0040-4039(00)85436-2

Reference yield:

(S)-methyl 2-amino-3-(6-methoxy-1H-indol-3-yl)propanoate (107447-04-1) → fumitremorgin B (111139-38-9,12626-17-4)

Guidance literature:

Multi-step reaction with 9 steps

1: 2.) Lawesson's reagent

2: 1.) MeI; 2.) NaBH₄

3: 92 percent / triethylamine / CH₂Cl₂ / 2 h / Ambient temperature

4: 23 percent / DDQ / CCl₄; CHCl₃ / 1.83 h / -10 deg C to room temperature

5: 1.) 85percent MCPBA, NaHCO₃ / 1.) CH₂Cl₂, 0 deg C, 10 min, 2.) toluene, reflux, 40 min

6: 84 percent / Zn / methanol / 0.5 h / Heating

7: 77 percent / NBS / tetrahydrofuran; H₂O / 0.17 h / 0 °C

8: 65 percent / KOH, 18-crown-6 / benzene / 1.67 h / Ambient temperature

9: 1.) DDQ; 2.) NaBH₄ / 1.) CH₃CN, H₂O, 70 deg C, 60 min; 2.) MeOH, 0 deg C, 8 min

With Lawessons reagent; potassium hydroxide; sodium tetrahydroborate; N-Bromosuccinimide; 18-crown-6 ether; sodium hydrogencarbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; zinc; methyl iodide; In tetrahydrofuran; methanol; tetrachloromethane; dichloromethane; chloroform; water; benzene;

DOI:10.1016/S0040-4020(01)85828-2

Reference yield:

C22H23N3O3 (111447-54-2) → fumitremorgin B (111139-38-9,12626-17-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 77 percent / NBS / tetrahydrofuran; H₂O / 0.17 h / 0 °C

2: 65 percent / KOH, 18-crown-6 / benzene / 1.67 h / Ambient temperature

3: 1.) DDQ; 2.) NaBH₄ / 1.) CH₃CN, H₂O, 70 deg C, 60 min; 2.) MeOH, 0 deg C, 8 min

With potassium hydroxide; sodium tetrahydroborate; N-Bromosuccinimide; 18-crown-6 ether; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; water; benzene;

DOI:10.1016/S0040-4020(01)85828-2

upstream raw materials:

13-oxofumitremorgin B

13-epi-fumitremorgin B

12,13-Dihydroxyfumitremorgin C

3,3-dimethyl-allyl chloride

Downstream raw materials:

verruculogen

13-oxoverruculogen

12,13-Dihydroxyfumitremorgin C

Refernces

• 1、 Kodato,Nakagawa,Hongu,Kawate,Hino. "Total synthesis of (+)-fumitremorgin b, its epimeric isomers, and demethoxy derivatives". . p. 359 - 377. Retrieved 2007/10/02.
• 2、 Nakagawa,Kodato,Hongu,et al.. "Total synthesis of fumitremorgin B". . p. 6217 - 6220. Retrieved 2007/10/02.