Fumitremorgin A

Base Information

Chemical Name:Fumitremorgin A
CAS No.:12626-18-5
Molecular Formula:C₃₂H₄₁N₃O₇
Molecular Weight:579.693
Hs Code.:
UNII:ZR1C7949XT
DSSTox Substance ID:DTXSID30925479
Wikidata:Q27140132
Metabolomics Workbench ID:66106
Mol file:12626-18-5.mol

Synonyms:Fumitremorgin A;Fumitremorgin A, 5S-(5alpha,10beta,10abeta,14aalpha,15balpha)-isomer

Suppliers and Price of Fumitremorgin A

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

American Custom Chemicals Corporation
FUMITREMORGIN A 95.00%
5MG
$ 504.75

Total 6 raw suppliers

Chemical Property of Fumitremorgin A

Chemical Property:

Vapor Pressure:2.03E-24mmHg at 25°C
Boiling Point:762.1°Cat760mmHg
Flash Point:414.7°C
PSA：102.70000
Density:1.34g/cm³
LogP:4.72140
XLogP3:3.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:5
Exact Mass:579.29445066
Heavy Atom Count:42
Complexity:1150

Purity/Quality:

99% ^*data from raw suppliers

FUMITREMORGIN A 95.00% ^*data from reagent suppliers

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Canonical SMILES:CC(=CCOC1C2=C3C(CC(OOC(N3C4=C2C=CC(=C4)OC)C=C(C)C)(C)C)N5C1(C(=O)N6CCCC6C5=O)O)C
Isomeric SMILES:CC(=CCO[C@H]1C2=C3[C@H](CC(OO[C@@H](N3C4=C2C=CC(=C4)OC)C=C(C)C)(C)C)N5[C@@]1(C(=O)N6CCC[C@H]6C5=O)O)C

Technology Process of Fumitremorgin A

There total 19 articles about Fumitremorgin A 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: 95.0%

: 12771-72-1
verruculogen

: 870-63-3
prenyl bromide

: 12626-18-5
Fumitremorgin A

Guidance literature:: With tetra-(n-butyl)ammonium iodide; di(n-butyl)tin oxide; In 1,2-dichloro-ethane; at 23 ℃; for 17h; Inert atmosphere;
DOI:10.1021/jacs.5b07154

Reference yield:

: 141215-69-2,33900-28-6
methyl (2S)-2-{[(tert-butoxy)carbonyl]amino}-3-(1H-indol-3-yl)propanoate

: 12626-18-5
Fumitremorgin A

Guidance literature:: Multi-step reaction with 13 steps

1.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

1.2: 1 h / -78 - 23 °C / Inert atmosphere

2.1: (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 1,10-Phenanthroline; bis(pinacol)diborane; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane / hexane / 24 h / 80 °C / Inert atmosphere; Sealed tube

2.2: 36 h / 23 °C / Inert atmosphere; Sealed tube

3.1: hydrogenchloride / water; ethyl acetate / 3 h / 60 °C / Inert atmosphere

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 23 °C / Inert atmosphere

5.1: chloroform / 1 h / 0 °C / Inert atmosphere; Molecular sieve

6.1: trifluoroacetic acid / 24 h / 0 °C / Inert atmosphere

7.1: sodium hydrogencarbonate / dichloromethane; water / 5 h / 23 °C / Inert atmosphere

8.1: Nitrosobenzene; zirconium(IV) chloride / dichloromethane / 3 h / 0 - 23 °C / Inert atmosphere

9.1: diethylamine / tetrahydrofuran / 40 °C / Inert atmosphere

10.1: osmium(VIII) oxide; 4-methyl-morpholine / water; acetonitrile; tert-butyl alcohol; acetone / 8 h / 23 °C / Inert atmosphere

11.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran; N,N-dimethyl-formamide / 0.17 h / 0 °C / Inert atmosphere

12.1: boron trifluoride diethyl etherate / 1,2-dichloro-ethane / 0.25 h / -20 °C / Inert atmosphere; Molecular sieve

13.1: tetra-(n-butyl)ammonium iodide; di(n-butyl)tin oxide / 1,2-dichloro-ethane / 17 h / 23 °C / Inert atmosphere

With 4-methyl-morpholine; hydrogenchloride; osmium(VIII) oxide; 1,10-Phenanthroline; (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; zirconium(IV) chloride; tetra-(n-butyl)ammonium iodide; di(n-butyl)tin oxide; sodium hydrogencarbonate; acetic acid; diethylamine; Nitrosobenzene; trifluoroacetic acid; bis(pinacol)diborane; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane; lithium hexamethyldisilazane; In tetrahydrofuran; hexane; dichloromethane; chloroform; water; ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetone; acetonitrile; tert-butyl alcohol; 5.1: |Pictet-Spengler Synthesis / 6.1: |Pictet-Spengler Synthesis;
DOI:10.1021/jacs.5b07154

Reference yield:

: (S)-methyl 2-((tert-butoxycarbonyl)amino)-3-(6-methoxy-1-(triisopropylsilyl)-1H-indol-3-yl)propanoate

: 12626-18-5
Fumitremorgin A

Guidance literature:: Multi-step reaction with 11 steps

1: hydrogenchloride / water; ethyl acetate / 3 h / 60 °C / Inert atmosphere

2: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 23 °C / Inert atmosphere

3: chloroform / 1 h / 0 °C / Inert atmosphere; Molecular sieve

4: trifluoroacetic acid / 24 h / 0 °C / Inert atmosphere

5: sodium hydrogencarbonate / dichloromethane; water / 5 h / 23 °C / Inert atmosphere

6: Nitrosobenzene; zirconium(IV) chloride / dichloromethane / 3 h / 0 - 23 °C / Inert atmosphere

7: diethylamine / tetrahydrofuran / 40 °C / Inert atmosphere

8: osmium(VIII) oxide; 4-methyl-morpholine / water; acetonitrile; tert-butyl alcohol; acetone / 8 h / 23 °C / Inert atmosphere

9: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran; N,N-dimethyl-formamide / 0.17 h / 0 °C / Inert atmosphere

10: boron trifluoride diethyl etherate / 1,2-dichloro-ethane / 0.25 h / -20 °C / Inert atmosphere; Molecular sieve

11: tetra-(n-butyl)ammonium iodide; di(n-butyl)tin oxide / 1,2-dichloro-ethane / 17 h / 23 °C / Inert atmosphere

With 4-methyl-morpholine; hydrogenchloride; osmium(VIII) oxide; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; zirconium(IV) chloride; tetra-(n-butyl)ammonium iodide; di(n-butyl)tin oxide; sodium hydrogencarbonate; acetic acid; diethylamine; Nitrosobenzene; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; chloroform; water; ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetone; acetonitrile; tert-butyl alcohol; 3: |Pictet-Spengler Synthesis / 4: |Pictet-Spengler Synthesis;
DOI:10.1021/jacs.5b07154