Fuligorubin A

CAS# 108343-55-1

Fuligorubin A

2D Structure

Catalog No. BCN1837----Order now to get a substantial discount!

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Fuligorubin A

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Chemical Properties of Fuligorubin A

Cas No. 108343-55-1 SDF Download SDF
PubChem ID 102328490 Appearance Red cryst.
Formula C20H23NO5 M.Wt 357.40
Type of Compound Alkaloids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name 3-[(2R)-4-[(2E,4E,6E,8E,10E)-1-hydroxydodeca-2,4,6,8,10-pentaenylidene]-1-methyl-3,5-dioxopyrrolidin-2-yl]propanoic acid
SMILES CC=CC=CC=CC=CC=CC(=C1C(=O)C(N(C1=O)C)CCC(=O)O)O
Standard InChIKey VRWPPQTYMAFCLL-STUTZMFMSA-N
Standard InChI InChI=1S/C20H23NO5/c1-3-4-5-6-7-8-9-10-11-12-16(22)18-19(25)15(13-14-17(23)24)21(2)20(18)26/h3-12,15,22H,13-14H2,1-2H3,(H,23,24)/b4-3+,6-5+,8-7+,10-9+,12-11+,18-16?/t15-/m1/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Fuligorubin A

The Topsentia roquensis

Protocol of Fuligorubin A

Structure Identification
Tetrahedron,1992,48(6): 1145–1174.

Further reactions of t-butyl 3-oxobutanthioate and t-butyl 4-diethyl-phosphono-3-oxobutanthioate : Carbonyl coupling reactions, amination, use in the preparation of 3-acyltetramic acids and application to the total synthesis of fuligorubin A.[Reference: WebLink]


METHODS AND RESULTS:
The use of t-butyl-3-oxobutanthioate (1) and t-butyl 4-diethylphosphono-3-oxobutanthioate (2) for the preparation of homologated derivatives suitable for amination in the presence of silver (I) trifluoroacetate to afford the corresponding β-ketoamides is discussed. In particular Wadsworth-Emmons coupling reactions of (2) with various carbonyl compounds gave good yields of E-substituted products.
CONCLUSIONS:
Many of the β-ketoamides were shown to be suitable precursors for 3-acyltetramic acids using a Dieckmann cyclisation with tetra-n-butyl ammonium fluoride as the cyclising base. These new reactions were applied to the total synthesis of the polyene 3-acyltetramic acid Fuligorubin A.

Tetrahedron Letters,1988,29(45):5829–5832.

Use of t-butyl 4-diethylphosphono-3-oxobutanethioate for tetramic acid synthesis: Total synthesis of the plasmodial pigment fuligorubin A[Reference: WebLink]


METHODS AND RESULTS:
A short, efficient synthesis of the yellow slime mould pigment Fuligorubin A (1) has been achieved using coupling of t-butyl 4-diethylphosphono-3-oxobutanethioate with deca-2,4,6,8-tetraenal and subsequent substitution with a glutamic acid derivative followed by Dieckmann cyclisation.

Fuligorubin A Dilution Calculator

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Fuligorubin A Molarity Calculator

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Preparing Stock Solutions of Fuligorubin A

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.798 mL 13.9899 mL 27.9799 mL 55.9597 mL 69.9496 mL
5 mM 0.5596 mL 2.798 mL 5.596 mL 11.1919 mL 13.9899 mL
10 mM 0.2798 mL 1.399 mL 2.798 mL 5.596 mL 6.995 mL
50 mM 0.056 mL 0.2798 mL 0.5596 mL 1.1192 mL 1.399 mL
100 mM 0.028 mL 0.1399 mL 0.2798 mL 0.5596 mL 0.6995 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Fuligorubin A

Further reactions of t-butyl 3-oxobutanthioate and t-butyl 4-diethyl-phosphono-3-oxobutanthioate : Carbonyl coupling reactions, amination, use in the preparation of 3-acyltetramic acids and application to the total synthesis of fuligorubin A.

Tetrahedron Volume 48, Issue 6, 1992, Pages 1145–1174

The use of t-butyl-3-oxobutanthioate (1) and t-butyl 4-diethylphosphono-3-oxobutanthioate (2) for the preparation of homologated derivatives suitable for amination in the presence of silver (I) trifluoroacetate to afford the corresponding β-ketoamides is discussed. In particular Wadsworth-Emmons coupling reactions of (2) with various carbonyl compounds gave good yields of E-substituted products. Many of the β-ketoamides were shown to be suitable precursors for 3-acyltetramic acids using a Dieckmann cyclisation with tetra-n-butyl ammonium fluoride as the cyclising base. These new reactions were applied to the total synthesis of the polyene 3-acyltetramic acid Fuligorubin A.

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