25999-31-9

Basic information

• Product Name: Lasalocid
• Synonyms: Lasalocid;[2R-[2alpha[2S*(3R*,4S*,5S*,7R*)3S*,5S*],5alpha,6beta]]-6-[7-[5-ethyl-5-(5-ethyltetrahydro-5-hydroxy-6-methyl-2H-pyran-2-yl)tetrahydro-3-methyl-2-furyl]-4-hydroxy-3,5-dimethyl-6-oxononyl]-3-methylsalicylic acid;Benzoic acid, 6-(3R,4S,5S,7R)-7-(2S,3S,5S)-5-ethyl-5-(2R,5R,6S)-5-ethyltetrahydro-5-hydroxy-6-methyl-2H-pyran-2-yltetrahydro-3-methyl-2-furanyl-4-hydroxy-3,5-dimethyl-6-oxononyl-2-hydroxy-3-methyl-;Lasalocid A;25999-20-6 (Sodium salt);6-{7-[(5S)-5-((6S,5R)-5-Ethyl-5-hydroxy-6-methylperhydro-2H-pyran-2-yl)-5-ethyl-3-methyloxolan-2-yl](4S,5S,3R,7R)-4-hydroxy-3,5-dimethyl-6-oxononyl}-2-hydroxy-3-methylbenzoic acid;Aids003766;Aids-003766
• CAS NO: 25999-31-9
• Molecular Formula: C₃₄H₅₄O₈
• Molecular Weight: 590.78776
• EINECS: 247-401-9
• Mol File: 25999-31-9.mol
• Article Data: 9

Chemical Properties

• Melting Point: 110-114°; mp 100-109° (unsharp)
• Boiling Point: 735.7°Cat760mmHg
• Flash Point: 224.8°C
• Appearance: /
• Density: 1.119g/cm³
• Vapor Pressure: 1.01E-22mmHg at 25°C
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility: Acetonitrile,(Slightly), Methanol (Slightly, Sonicated)
• PKA: 3.15±0.39(Predicted)
• CAS DataBase Reference: Lasalocid(CAS DataBase Reference)
• NIST Chemistry Reference: Lasalocid(25999-31-9)
• EPA Substance Registry System: Lasalocid(25999-31-9)

Safety Data

• Hazardous Substances Data: 25999-31-9(Hazardous Substances Data)

Usage

Description

Lasalocid is an ionophore antibiotic isolated from Streptomyces lasaliensis, characterized by its potent antibacterial activity and the ability to form neutral complexes with monovalent and divalent cations, as well as larger organic cations like protonated dopamine. It is used in veterinary practice as a coccidiostat for gastrointestinal parasites and has demonstrated cytotoxicity targeting cell metabolism.

Uses

Used in Veterinary Medicine:
Lasalocid is used as a coccidiostat for treating gastrointestinal parasites in animals. It is effective in controlling coccidiosis, a disease caused by protozoan parasites of the genus Eimeria, which can lead to significant economic losses in poultry farming.
Used in Anticancer Applications:
Lasalocid functions as an anticancer supplement agent, particularly for treating brain tumors. It comprises a polyether antibiotic that inhibits mitochondrial GPD2 activity, leading to anti-proliferative effects on cancer cells.
Used in Pharmaceutical Research:
Lasalocid's unique ability to transport ions through apolar phases, including lipid bilayer membranes, makes it a valuable tool in pharmaceutical research. Its properties are being studied for potential applications in drug delivery and the development of new therapeutic agents.
Brand Names:
Avatec [as sodium] [Veterinary] (Hoffmann-LaRoche)
Bovatec [as sodium] [Veterinary] (Hoffmann-LaRoche)

in vitro

a previous study was conducted to compare effects of the combined use of lasalocid and silybin in chicken hepatoma cells and rat myoblasts cell lines cultures. results showed that in all performed tests, the lowest lasalocid ec50-values were obtained for chicken hepatocytes. in the rat myoblasts cultures, the lowest lasalocid ec50-values were found. moreover, a lack of silybin cytotoxic effect was proven for the studied cell lines. an interaction between both substances resulted in a great decrease of lasalocid cytotoxicity. the isobolograms and combination index indicated a significant antagonistic nature of silybin effect in the course of lasalocid cytotoxicity [1].

in vivo

in a animal study, chickens 8 or 9 days old were given a completely purified crystalline amino acid diet. results showed that the requirement for sulphur-containing amino acids (saa) was neither increased nor decreased by lasalocid at 125 mg/kg diet. moreover, lasalocid could cause a significant increase in gain and gain/feed intake when added to diets that were deficient in saa, but it led to a marked decrease in performance when added to diets adequate in saa. in addition, at moderate levels of saa deficiency, lasalocid at 125 mg/kg could neither increase nor decrease the rate and efficiency of weight gain and there was no evidence of the saa x lasalocid interaction when lasalocid was given in a typical starter diet of maize and soya [2].

references

[1] radko, l. ,cybulski, w., and rzeski, w. the protective effect of silybin against lasalocid cytotoxic exposure on chicken and rat cell lines. biomed.res.int. 2013, 1-8 (2013).[2] willis gm, baker dh. lasalocid-sulfur amino acid interrelationship in the chick. poult sci. 1980 nov;59(11):2538-43.

InChI:InChI=1/C34H54O8.Na/c1-9-25(31-21(6)18-34(11-3,42-31)26-16-17-33(40,10-2)23(8)41-26)30(37)22(7)28(35)19(4)12-14-24-15-13-20(5)29(36)27(24)32(38)39;/h13,15,19,21-23,25-26,28,31,35-36,40H,9-12,14,16-18H2,1-8H3,(H,38,39);/q;+1/p-1/t19-,21+,22?,23+,25+,26?,28+,31?,33-,34?;/m1./s1

Synthetic route

lasalocid benzyl ester (41733-86-2) → lasalocid (X 537 A) (25999-31-9)

Conditions	Yield
With hydrogen; palladium dihydroxide In ethanol Ambient temperature; Yield given;
With hydrogen; palladium on activated charcoal In ethanol for 3h; Ambient temperature;

3-methyl-6-(3(R)-formylbutyl)salicylic acid benzyl ester (67045-68-5) → lasalocid (X 537 A) (25999-31-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 33.8 percent / LDA, ZnCl2 / diethyl ether / 0 °C 2: H2 / palladium on carbon / ethanol / 3 h / Ambient temperature View Scheme

lasalocid sodium (25999-20-6) → lasalocid (X 537 A) (25999-31-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: dioxane 2: H2 / palladium on carbon / ethanol / 3 h / Ambient temperature View Scheme
With sulfuric acid; water In dichloromethane pH=1.5;
With sulfuric acid In dichloromethane; water pH=1.5;
With sulfuric acid In dichloromethane; water	0.75 g

(2S)-2-<(2S,3S,5S)-5-ethyl-5-<(2R,5R,6S)-5-ethyl-5-hydroxy-6-methyltetrahydropyran-2-yl>-3-methyltetrahydrofur-2-yl>butan-1-ol (73657-53-1) → lasalocid (X 537 A) (25999-31-9)

Conditions	Yield
Multi-step reaction with 5 steps 1: 78 percent / sodium acetate, pyridinium chlorochromate / CH2Cl2 / 2 h 2: 89 percent / tetrahydrofuran / 0.5 h / 0 °C 3: 90 percent / sodium acetate, pyridinium chlorochromate / CH2Cl2 / 2 h 4: 33.8 percent / LDA, ZnCl2 / diethyl ether / 0 °C 5: H2 / palladium on carbon / ethanol / 3 h / Ambient temperature View Scheme
Multi-step reaction with 5 steps 1: 84 percent / PCC, 3A-MS / CH2Cl2 / Ambient temperature 2: tetrahydrofuran / 0 °C 3: PCC, 3A-MS / CH2Cl2 / Ambient temperature 5: H2 / Pd(OH)2 / ethanol / Ambient temperature View Scheme

(3RS,4S)-4-<(2S,3S,5S)-5-ethyl-5-<(2R,5R,6S)-5-ethyl-5-hydroxy-6-methyltetrahydropyran-2-yl>-3-methyltetrahydrofur-2-yl>hexan-3-ol (84911-92-2, 84985-23-9, 87678-43-1, 87678-51-1) → lasalocid (X 537 A) (25999-31-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: 90 percent / sodium acetate, pyridinium chlorochromate / CH2Cl2 / 2 h 2: 33.8 percent / LDA, ZnCl2 / diethyl ether / 0 °C 3: H2 / palladium on carbon / ethanol / 3 h / Ambient temperature View Scheme
Multi-step reaction with 3 steps 1: PCC, 3A-MS / CH2Cl2 / Ambient temperature 3: H2 / Pd(OH)2 / ethanol / Ambient temperature View Scheme

(2R)-2-<(2S,3S,5S)-5-ethyl-5-<(2R,5R,6S)-5-ethyl-5-hydroxy-6-methyltetrahydropyran-2-yl>-3-methyltetrahydrofur-2-yl>butanal (84911-91-1) → lasalocid (X 537 A) (25999-31-9)

Conditions	Yield
Multi-step reaction with 4 steps 1: 89 percent / tetrahydrofuran / 0.5 h / 0 °C 2: 90 percent / sodium acetate, pyridinium chlorochromate / CH2Cl2 / 2 h 3: 33.8 percent / LDA, ZnCl2 / diethyl ether / 0 °C 4: H2 / palladium on carbon / ethanol / 3 h / Ambient temperature View Scheme
Multi-step reaction with 4 steps 1: tetrahydrofuran / 0 °C 2: PCC, 3A-MS / CH2Cl2 / Ambient temperature 4: H2 / Pd(OH)2 / ethanol / Ambient temperature View Scheme

4(R)-<5(S)-ethyl-3(S)-methyl-5-(5(R)-ethyl-5-hydroxy-6(S)-methyl-2(R)-tetrahydropyranyl)-2(S)-tetrahydrofuryl>hexan-3-one (31478-26-9, 87678-18-0) → lasalocid (X 537 A) (25999-31-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 33.8 percent / LDA, ZnCl2 / diethyl ether / 0 °C 2: H2 / palladium on carbon / ethanol / 3 h / Ambient temperature View Scheme
Multi-step reaction with 2 steps 2: H2 / Pd(OH)2 / ethanol / Ambient temperature View Scheme

3-methyl-6-(3(R)-methyl-4,5-O-isopropylidenepentyl)salicylic acid methyl ester (75371-81-2, 84911-50-2, 84911-98-8) → lasalocid (X 537 A) (25999-31-9)

Conditions

Yield

Multi-step reaction with 6 steps 1: KH / tetrahydrofuran / 1.) 0 deg C, 20 min, 2.) 0 deg C, 1 h, 3.) room temperature, 0.5 h 2: 1.) BuLi, n-propanethiol / 1.) pentane, hexane, 0 deg C, 15 min, 2.) HMPA, 0 deg C, 10 min, room temperature, 45 min, 3.) room temperature, 2 h 3: 10percent HCl / H2O; tetrahydrofuran / 1.) room temperature, 4 h, 2.) 50 deg C, 7 h 4: 80 percent / NaIO4 / methanol; H2O / 2 h / Ambient temperature 5: 33.8 percent / LDA, ZnCl2 / diethyl ether / 0 °C 6: H2 / palladium on carbon / ethanol / 3 h / Ambient temperature View Scheme

benzyl 2(S)-<5(S)-ethyl-3(S)-methyl-5-(5(R)-ethyl-5-hydroxy-6(S)-methyl-2(R)-tetrahydropyranyl)-2(S)-tetrahydrofuryl>butyl ether (73657-51-9) → lasalocid (X 537 A) (25999-31-9)

Conditions

Yield

Multi-step reaction with 10 steps 1: 94 percent / oxalyl chloride, dimethyl sulfoxide, Et3N / CH2Cl2 / 1.) -60 deg C, 10 min, 2.) 15 min, 3.) warm to room temperature 2: 94 percent / n-BuLi / tetrahydrofuran; hexane / 1.) room temperature, 1 h, 2.) -78 deg C to room temperature, 10 h 3: NaHCO3, MCPBA / CH2Cl2 / 3 h / Ambient temperature 4: 90 percent / CuI / pentane; diethyl ether / 1.) 0 deg C, 15 min, 2.) 3 h 5: 98 percent / Li, NH3 / tetrahydrofuran / 1 h / Heating 6: 78 percent / sodium acetate, pyridinium chlorochromate / CH2Cl2 / 2 h 7: 89 percent / tetrahydrofuran / 0.5 h / 0 °C 8: 90 percent / sodium acetate, pyridinium chlorochromate / CH2Cl2 / 2 h 9: 33.8 percent / LDA, ZnCl2 / diethyl ether / 0 °C 10: H2 / palladium on carbon / ethanol / 3 h / Ambient temperature View Scheme

benzyl 2(S)-<5(S)-ethyl-3(S)-methyl-5-(3(R)-1,5-dioxo-4(S)-methylspiro<2.5>-6(R)-octyl)-2(S)-tetrahydrofuryl>butyl ether (73657-52-0) → lasalocid (X 537 A) (25999-31-9)

Conditions

Yield

Multi-step reaction with 7 steps 1: 90 percent / CuI / pentane; diethyl ether / 1.) 0 deg C, 15 min, 2.) 3 h 2: 98 percent / Li, NH3 / tetrahydrofuran / 1 h / Heating 3: 78 percent / sodium acetate, pyridinium chlorochromate / CH2Cl2 / 2 h 4: 89 percent / tetrahydrofuran / 0.5 h / 0 °C 5: 90 percent / sodium acetate, pyridinium chlorochromate / CH2Cl2 / 2 h 6: 33.8 percent / LDA, ZnCl2 / diethyl ether / 0 °C 7: H2 / palladium on carbon / ethanol / 3 h / Ambient temperature View Scheme

2-(dibenzylamino)-3-methyl-6-(3(R)-methyl-4-pentenyl)benzoic acid methyl ester (75371-80-1) → lasalocid (X 537 A) (25999-31-9)

Conditions

Yield

Multi-step reaction with 10 steps 1: 91 percent / 4-methylmorpholine 4-oxide, OsO4 / H2O; 2-methyl-propan-2-ol / 24 h / Ambient temperature 2: 93 percent / H2 / Pd/C / ethanol / 10 h / 2585.7 Torr 3: 85 percent / HBF4, isoamyl nitrite / ethanol / 0.5 h / 0 °C 4: 98 percent / p-toluenesulfonic acid / acetone / 0.25 h / Ambient temperature 5: KH / tetrahydrofuran / 1.) 0 deg C, 20 min, 2.) 0 deg C, 1 h, 3.) room temperature, 0.5 h 6: 1.) BuLi, n-propanethiol / 1.) pentane, hexane, 0 deg C, 15 min, 2.) HMPA, 0 deg C, 10 min, room temperature, 45 min, 3.) room temperature, 2 h 7: 10percent HCl / H2O; tetrahydrofuran / 1.) room temperature, 4 h, 2.) 50 deg C, 7 h 8: 80 percent / NaIO4 / methanol; H2O / 2 h / Ambient temperature 9: 33.8 percent / LDA, ZnCl2 / diethyl ether / 0 °C 10: H2 / palladium on carbon / ethanol / 3 h / Ambient temperature View Scheme

benzyl 2(S)-<5(S)-carbomethoxy-3(S)-methyl-5-(5,6-dihydro)-5(S)-(methoxymethylenoxy)-6(S)-methyl-2(R)-pyranyl-2(S)-tetrahydrofuryl>butyl ether (84985-06-8) → lasalocid (X 537 A) (25999-31-9)

Conditions

Yield

Multi-step reaction with 15 steps 1: 85 percent / H2 / Ni(Ra) / ethyl acetate / 3 h / Ambient temperature 2: 95 percent / DIBAL / diethyl ether; hexane / 1 h / -78 °C 3: 88 percent / n-BuLi / tetrahydrofuran; hexane / 1.) room temperature, 1 h, 2.) -78 deg C to room temperature, 10 h 4: 90 percent / H2 / Ni(Ra) / ethyl acetate / 3 h / Ambient temperature 5: 100 percent / 10percent HCl / tetrahydrofuran; H2O / 16 h / 50 °C 6: 94 percent / oxalyl chloride, dimethyl sulfoxide, Et3N / CH2Cl2 / 1.) -60 deg C, 10 min, 2.) 15 min, 3.) warm to room temperature 7: 94 percent / n-BuLi / tetrahydrofuran; hexane / 1.) room temperature, 1 h, 2.) -78 deg C to room temperature, 10 h 8: NaHCO3, MCPBA / CH2Cl2 / 3 h / Ambient temperature 9: 90 percent / CuI / pentane; diethyl ether / 1.) 0 deg C, 15 min, 2.) 3 h 10: 98 percent / Li, NH3 / tetrahydrofuran / 1 h / Heating 11: 78 percent / sodium acetate, pyridinium chlorochromate / CH2Cl2 / 2 h 12: 89 percent / tetrahydrofuran / 0.5 h / 0 °C 13: 90 percent / sodium acetate, pyridinium chlorochromate / CH2Cl2 / 2 h 14: 33.8 percent / LDA, ZnCl2 / diethyl ether / 0 °C 15: H2 / palladium on carbon / ethanol / 3 h / Ambient temperature View Scheme

3-methyl-6-(3(R)-methyl-4,5-dihydroxypentyl)salicylic acid methyl ester (75371-88-9, 84911-49-9, 84911-97-7) → lasalocid (X 537 A) (25999-31-9)

Conditions

Yield

Multi-step reaction with 7 steps 1: 98 percent / p-toluenesulfonic acid / acetone / 0.25 h / Ambient temperature 2: KH / tetrahydrofuran / 1.) 0 deg C, 20 min, 2.) 0 deg C, 1 h, 3.) room temperature, 0.5 h 3: 1.) BuLi, n-propanethiol / 1.) pentane, hexane, 0 deg C, 15 min, 2.) HMPA, 0 deg C, 10 min, room temperature, 45 min, 3.) room temperature, 2 h 4: 10percent HCl / H2O; tetrahydrofuran / 1.) room temperature, 4 h, 2.) 50 deg C, 7 h 5: 80 percent / NaIO4 / methanol; H2O / 2 h / Ambient temperature 6: 33.8 percent / LDA, ZnCl2 / diethyl ether / 0 °C 7: H2 / palladium on carbon / ethanol / 3 h / Ambient temperature View Scheme

2(S)-<5(S)-ethyl-3(S)-methyl-5-(5(R)-ethyl-5-(trimethylsiloxy)-6(S)-methyl-2(R)-tetrahydropyranyl)-2(S)-tetrahydrofuryl>butan-1-ol (84911-36-4) → lasalocid (X 537 A) (25999-31-9)

Conditions

Yield

Multi-step reaction with 6 steps 1: 92 percent / n-Bu4NF / tetrahydrofuran / 4 h 2: 78 percent / sodium acetate, pyridinium chlorochromate / CH2Cl2 / 2 h 3: 89 percent / tetrahydrofuran / 0.5 h / 0 °C 4: 90 percent / sodium acetate, pyridinium chlorochromate / CH2Cl2 / 2 h 5: 33.8 percent / LDA, ZnCl2 / diethyl ether / 0 °C 6: H2 / palladium on carbon / ethanol / 3 h / Ambient temperature View Scheme

2-amino-3-methyl-6-(3(R)-methyl-4,5-O-isopropylidenepentyl)benzoic acid methyl ester (75371-87-8, 84911-48-8, 84911-96-6) → lasalocid (X 537 A) (25999-31-9)

Conditions

Yield

Multi-step reaction with 8 steps 1: 85 percent / HBF4, isoamyl nitrite / ethanol / 0.5 h / 0 °C 2: 98 percent / p-toluenesulfonic acid / acetone / 0.25 h / Ambient temperature 3: KH / tetrahydrofuran / 1.) 0 deg C, 20 min, 2.) 0 deg C, 1 h, 3.) room temperature, 0.5 h 4: 1.) BuLi, n-propanethiol / 1.) pentane, hexane, 0 deg C, 15 min, 2.) HMPA, 0 deg C, 10 min, room temperature, 45 min, 3.) room temperature, 2 h 5: 10percent HCl / H2O; tetrahydrofuran / 1.) room temperature, 4 h, 2.) 50 deg C, 7 h 6: 80 percent / NaIO4 / methanol; H2O / 2 h / Ambient temperature 7: 33.8 percent / LDA, ZnCl2 / diethyl ether / 0 °C 8: H2 / palladium on carbon / ethanol / 3 h / Ambient temperature View Scheme

(2S,6R)-6-[(2S,4S,5S)-5-((S)-1-Benzyloxymethyl-propyl)-2-ethyl-4-methyl-tetrahydro-furan-2-yl]-3-eth-(Z)-ylidene-2-methyl-tetrahydro-pyran (84911-38-6) → lasalocid (X 537 A) (25999-31-9)

Conditions

Yield

Multi-step reaction with 11 steps 1: 1.) O3, 2.) NaBH4 / 1.) CH3OH, CH2Cl2, -78 deg C, 2.) room temperature, 10 h 2: 94 percent / oxalyl chloride, dimethyl sulfoxide, Et3N / CH2Cl2 / 1.) -60 deg C, 10 min, 2.) 15 min, 3.) warm to room temperature 3: 94 percent / n-BuLi / tetrahydrofuran; hexane / 1.) room temperature, 1 h, 2.) -78 deg C to room temperature, 10 h 4: NaHCO3, MCPBA / CH2Cl2 / 3 h / Ambient temperature 5: 90 percent / CuI / pentane; diethyl ether / 1.) 0 deg C, 15 min, 2.) 3 h 6: 98 percent / Li, NH3 / tetrahydrofuran / 1 h / Heating 7: 78 percent / sodium acetate, pyridinium chlorochromate / CH2Cl2 / 2 h 8: 89 percent / tetrahydrofuran / 0.5 h / 0 °C 9: 90 percent / sodium acetate, pyridinium chlorochromate / CH2Cl2 / 2 h 10: 33.8 percent / LDA, ZnCl2 / diethyl ether / 0 °C 11: H2 / palladium on carbon / ethanol / 3 h / Ambient temperature View Scheme

(R)-2-[(2S,3S,5S)-5-Ethyl-5-((2R,5R,6S)-5-ethyl-6-methyl-5-trimethylsilanyloxy-tetrahydro-pyran-2-yl)-3-methyl-tetrahydro-furan-2-yl]-butyric acid → lasalocid (X 537 A) (25999-31-9)

Conditions

Yield

Multi-step reaction with 8 steps 1: diethyl ether 2: 99 percent / LiAlH4 / diethyl ether / 1 h 3: 92 percent / n-Bu4NF / tetrahydrofuran / 4 h 4: 78 percent / sodium acetate, pyridinium chlorochromate / CH2Cl2 / 2 h 5: 89 percent / tetrahydrofuran / 0.5 h / 0 °C 6: 90 percent / sodium acetate, pyridinium chlorochromate / CH2Cl2 / 2 h 7: 33.8 percent / LDA, ZnCl2 / diethyl ether / 0 °C 8: H2 / palladium on carbon / ethanol / 3 h / Ambient temperature View Scheme

methyl 2(R)-<5(S)-ethyl-3(S)-methyl-5-(5(R)-ethyl-5-(trimethylsiloxy)-6(S)-methyl-2(R)-tetrahydropyranyl)-2(S)-tetrahydrofuryl>butanoate (84911-35-3) → lasalocid (X 537 A) (25999-31-9)

Conditions

Yield

Multi-step reaction with 7 steps 1: 99 percent / LiAlH4 / diethyl ether / 1 h 2: 92 percent / n-Bu4NF / tetrahydrofuran / 4 h 3: 78 percent / sodium acetate, pyridinium chlorochromate / CH2Cl2 / 2 h 4: 89 percent / tetrahydrofuran / 0.5 h / 0 °C 5: 90 percent / sodium acetate, pyridinium chlorochromate / CH2Cl2 / 2 h 6: 33.8 percent / LDA, ZnCl2 / diethyl ether / 0 °C 7: H2 / palladium on carbon / ethanol / 3 h / Ambient temperature View Scheme

2-(β-methoxyethoxymethyl)-3-methyl-6-(3(R)-methyl-4,5-O-isopropylidenepentyl)salicylic acid methyl ester (75371-89-0, 84911-51-3, 84911-99-9) → lasalocid (X 537 A) (25999-31-9)

Conditions

Yield

Multi-step reaction with 5 steps 1: 1.) BuLi, n-propanethiol / 1.) pentane, hexane, 0 deg C, 15 min, 2.) HMPA, 0 deg C, 10 min, room temperature, 45 min, 3.) room temperature, 2 h 2: 10percent HCl / H2O; tetrahydrofuran / 1.) room temperature, 4 h, 2.) 50 deg C, 7 h 3: 80 percent / NaIO4 / methanol; H2O / 2 h / Ambient temperature 4: 33.8 percent / LDA, ZnCl2 / diethyl ether / 0 °C 5: H2 / palladium on carbon / ethanol / 3 h / Ambient temperature View Scheme

2-(β-methoxyethoxymethyl)-3-methyl-6-(3(R)-methyl-4,5-O-isopropylidenepentyl)salicylic acid benzyl ester (84911-52-4, 84912-00-5) → lasalocid (X 537 A) (25999-31-9)

Conditions	Yield
Multi-step reaction with 4 steps 1: 10percent HCl / H2O; tetrahydrofuran / 1.) room temperature, 4 h, 2.) 50 deg C, 7 h 2: 80 percent / NaIO4 / methanol; H2O / 2 h / Ambient temperature 3: 33.8 percent / LDA, ZnCl2 / diethyl ether / 0 °C 4: H2 / palladium on carbon / ethanol / 3 h / Ambient temperature View Scheme

2-(dibenzylamino)-3-methyl-6-(3(R)-methyl-4,5-O-isopropylidenepentyl)benzoic acid methyl ester (75371-86-7, 84911-47-7, 84911-95-5) → lasalocid (X 537 A) (25999-31-9)

Conditions

Yield

Multi-step reaction with 9 steps 1: 93 percent / H2 / Pd/C / ethanol / 10 h / 2585.7 Torr 2: 85 percent / HBF4, isoamyl nitrite / ethanol / 0.5 h / 0 °C 3: 98 percent / p-toluenesulfonic acid / acetone / 0.25 h / Ambient temperature 4: KH / tetrahydrofuran / 1.) 0 deg C, 20 min, 2.) 0 deg C, 1 h, 3.) room temperature, 0.5 h 5: 1.) BuLi, n-propanethiol / 1.) pentane, hexane, 0 deg C, 15 min, 2.) HMPA, 0 deg C, 10 min, room temperature, 45 min, 3.) room temperature, 2 h 6: 10percent HCl / H2O; tetrahydrofuran / 1.) room temperature, 4 h, 2.) 50 deg C, 7 h 7: 80 percent / NaIO4 / methanol; H2O / 2 h / Ambient temperature 8: 33.8 percent / LDA, ZnCl2 / diethyl ether / 0 °C 9: H2 / palladium on carbon / ethanol / 3 h / Ambient temperature View Scheme

benzyl 2(S)-<5(S)-ethyl-3(S)-methyl-5-(6(S)-methyl-5-methylene-2(R)-tetrahydropyranyl)-2(S)-tetrahydrofuryl>butyl ether (84911-90-0) → lasalocid (X 537 A) (25999-31-9)

Conditions

Yield

Multi-step reaction with 8 steps 1: NaHCO3, MCPBA / CH2Cl2 / 3 h / Ambient temperature 2: 90 percent / CuI / pentane; diethyl ether / 1.) 0 deg C, 15 min, 2.) 3 h 3: 98 percent / Li, NH3 / tetrahydrofuran / 1 h / Heating 4: 78 percent / sodium acetate, pyridinium chlorochromate / CH2Cl2 / 2 h 5: 89 percent / tetrahydrofuran / 0.5 h / 0 °C 6: 90 percent / sodium acetate, pyridinium chlorochromate / CH2Cl2 / 2 h 7: 33.8 percent / LDA, ZnCl2 / diethyl ether / 0 °C 8: H2 / palladium on carbon / ethanol / 3 h / Ambient temperature View Scheme

benzyl 2(S)-<5(S)-ethyl-3(S)-methyl-5-(5(R)-ethyl-5-hydroxy-6(S)-methyl-2(R)-tetrahydropyranyl)-2(S)-tetrahydrofuryl>butyl ether (84911-37-5) → lasalocid (X 537 A) (25999-31-9)

Conditions	Yield
Multi-step reaction with 6 steps 1: 98 percent / Li, NH3 / tetrahydrofuran / 1 h / Heating 2: 78 percent / sodium acetate, pyridinium chlorochromate / CH2Cl2 / 2 h 3: 89 percent / tetrahydrofuran / 0.5 h / 0 °C 4: 90 percent / sodium acetate, pyridinium chlorochromate / CH2Cl2 / 2 h 5: 33.8 percent / LDA, ZnCl2 / diethyl ether / 0 °C 6: H2 / palladium on carbon / ethanol / 3 h / Ambient temperature View Scheme
Multi-step reaction with 12 steps 1: KH, CS2, CH3I / tetrahydrofuran / 1.) 5 h, 2.) 30 min 2: 1.) O3, 2.) NaBH4 / 1.) CH3OH, CH2Cl2, -78 deg C, 2.) room temperature, 10 h 3: 94 percent / oxalyl chloride, dimethyl sulfoxide, Et3N / CH2Cl2 / 1.) -60 deg C, 10 min, 2.) 15 min, 3.) warm to room temperature 4: 94 percent / n-BuLi / tetrahydrofuran; hexane / 1.) room temperature, 1 h, 2.) -78 deg C to room temperature, 10 h 5: NaHCO3, MCPBA / CH2Cl2 / 3 h / Ambient temperature 6: 90 percent / CuI / pentane; diethyl ether / 1.) 0 deg C, 15 min, 2.) 3 h 7: 98 percent / Li, NH3 / tetrahydrofuran / 1 h / Heating 8: 78 percent / sodium acetate, pyridinium chlorochromate / CH2Cl2 / 2 h 9: 89 percent / tetrahydrofuran / 0.5 h / 0 °C 10: 90 percent / sodium acetate, pyridinium chlorochromate / CH2Cl2 / 2 h 11: 33.8 percent / LDA, ZnCl2 / diethyl ether / 0 °C 12: H2 / palladium on carbon / ethanol / 3 h / Ambient temperature View Scheme

benzyl 2(S)-<5(S)-ethyl-3(S)-methyl-5-(6(S)-methyl-5-oxo-2(R)-tetrahydropyranyl)-2(S)-tetrahydrofuryl>butyl ether (84911-89-7, 87678-36-2) → lasalocid (X 537 A) (25999-31-9)

Conditions

Yield

Multi-step reaction with 9 steps 1: 94 percent / n-BuLi / tetrahydrofuran; hexane / 1.) room temperature, 1 h, 2.) -78 deg C to room temperature, 10 h 2: NaHCO3, MCPBA / CH2Cl2 / 3 h / Ambient temperature 3: 90 percent / CuI / pentane; diethyl ether / 1.) 0 deg C, 15 min, 2.) 3 h 4: 98 percent / Li, NH3 / tetrahydrofuran / 1 h / Heating 5: 78 percent / sodium acetate, pyridinium chlorochromate / CH2Cl2 / 2 h 6: 89 percent / tetrahydrofuran / 0.5 h / 0 °C 7: 90 percent / sodium acetate, pyridinium chlorochromate / CH2Cl2 / 2 h 8: 33.8 percent / LDA, ZnCl2 / diethyl ether / 0 °C 9: H2 / palladium on carbon / ethanol / 3 h / Ambient temperature View Scheme

3-methyl-6-(3(R)-methyl-4,5-dihydroxypentyl)salicylic acid benzyl ester (75371-90-3, 84911-53-5, 84912-01-6, 87598-86-5, 87599-04-0) → lasalocid (X 537 A) (25999-31-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: 80 percent / NaIO4 / methanol; H2O / 2 h / Ambient temperature 2: 33.8 percent / LDA, ZnCl2 / diethyl ether / 0 °C 3: H2 / palladium on carbon / ethanol / 3 h / Ambient temperature View Scheme

benzyl 2(S)-<5(S)-ethyl-3(S)-methyl-5-(5(S)-(methoxymethylenoxy)-6(S)-methyl-2(R)-tetrahydropyranyl)-2(S)-tetrahydrofuryl>butyl ether (84985-18-2) → lasalocid (X 537 A) (25999-31-9)

Conditions

Yield

Multi-step reaction with 11 steps 1: 100 percent / 10percent HCl / tetrahydrofuran; H2O / 16 h / 50 °C 2: 94 percent / oxalyl chloride, dimethyl sulfoxide, Et3N / CH2Cl2 / 1.) -60 deg C, 10 min, 2.) 15 min, 3.) warm to room temperature 3: 94 percent / n-BuLi / tetrahydrofuran; hexane / 1.) room temperature, 1 h, 2.) -78 deg C to room temperature, 10 h 4: NaHCO3, MCPBA / CH2Cl2 / 3 h / Ambient temperature 5: 90 percent / CuI / pentane; diethyl ether / 1.) 0 deg C, 15 min, 2.) 3 h 6: 98 percent / Li, NH3 / tetrahydrofuran / 1 h / Heating 7: 78 percent / sodium acetate, pyridinium chlorochromate / CH2Cl2 / 2 h 8: 89 percent / tetrahydrofuran / 0.5 h / 0 °C 9: 90 percent / sodium acetate, pyridinium chlorochromate / CH2Cl2 / 2 h 10: 33.8 percent / LDA, ZnCl2 / diethyl ether / 0 °C 11: H2 / palladium on carbon / ethanol / 3 h / Ambient temperature View Scheme

benzyl 2(S)-<5(R)-vinyl-3(S)-methyl-5-(5(S)-(methoxymethylenoxy)-6(S)-methyl-2(R)-tetrahydropyranyl)-2(S)-tetrahydrofuryl>butyl ether (84911-87-5, 84985-13-7, 84985-14-8, 84985-15-9, 87678-33-9) → lasalocid (X 537 A) (25999-31-9)

Conditions

Yield

Multi-step reaction with 12 steps 1: 90 percent / H2 / Ni(Ra) / ethyl acetate / 3 h / Ambient temperature 2: 100 percent / 10percent HCl / tetrahydrofuran; H2O / 16 h / 50 °C 3: 94 percent / oxalyl chloride, dimethyl sulfoxide, Et3N / CH2Cl2 / 1.) -60 deg C, 10 min, 2.) 15 min, 3.) warm to room temperature 4: 94 percent / n-BuLi / tetrahydrofuran; hexane / 1.) room temperature, 1 h, 2.) -78 deg C to room temperature, 10 h 5: NaHCO3, MCPBA / CH2Cl2 / 3 h / Ambient temperature 6: 90 percent / CuI / pentane; diethyl ether / 1.) 0 deg C, 15 min, 2.) 3 h 7: 98 percent / Li, NH3 / tetrahydrofuran / 1 h / Heating 8: 78 percent / sodium acetate, pyridinium chlorochromate / CH2Cl2 / 2 h 9: 89 percent / tetrahydrofuran / 0.5 h / 0 °C 10: 90 percent / sodium acetate, pyridinium chlorochromate / CH2Cl2 / 2 h 11: 33.8 percent / LDA, ZnCl2 / diethyl ether / 0 °C 12: H2 / palladium on carbon / ethanol / 3 h / Ambient temperature View Scheme

benzyl 2(S)-<5(S)-formyl-3(S)-methyl-5-(5(S)-(methoxymethylenoxy)-6(S)-methyl-2(R)-tetrahydropyranyl)-2(S)-tetrahydrofuryl>butyl ether (84985-12-6) → lasalocid (X 537 A) (25999-31-9)

Conditions

Yield

Multi-step reaction with 13 steps 1: 88 percent / n-BuLi / tetrahydrofuran; hexane / 1.) room temperature, 1 h, 2.) -78 deg C to room temperature, 10 h 2: 90 percent / H2 / Ni(Ra) / ethyl acetate / 3 h / Ambient temperature 3: 100 percent / 10percent HCl / tetrahydrofuran; H2O / 16 h / 50 °C 4: 94 percent / oxalyl chloride, dimethyl sulfoxide, Et3N / CH2Cl2 / 1.) -60 deg C, 10 min, 2.) 15 min, 3.) warm to room temperature 5: 94 percent / n-BuLi / tetrahydrofuran; hexane / 1.) room temperature, 1 h, 2.) -78 deg C to room temperature, 10 h 6: NaHCO3, MCPBA / CH2Cl2 / 3 h / Ambient temperature 7: 90 percent / CuI / pentane; diethyl ether / 1.) 0 deg C, 15 min, 2.) 3 h 8: 98 percent / Li, NH3 / tetrahydrofuran / 1 h / Heating 9: 78 percent / sodium acetate, pyridinium chlorochromate / CH2Cl2 / 2 h 10: 89 percent / tetrahydrofuran / 0.5 h / 0 °C 11: 90 percent / sodium acetate, pyridinium chlorochromate / CH2Cl2 / 2 h 12: 33.8 percent / LDA, ZnCl2 / diethyl ether / 0 °C 13: H2 / palladium on carbon / ethanol / 3 h / Ambient temperature View Scheme

benzyl 2(S)-<5(S)-carbomethoxy-3(S)-methyl-5-(5(S)-(methoxymethylenoxy)-6(S)-methyl-2(R)-tetrahydropyranyl)-2(S)-tetrahydrofuryl>butyl ether (84985-09-1) → lasalocid (X 537 A) (25999-31-9)

Conditions

Yield

Multi-step reaction with 14 steps 1: 95 percent / DIBAL / diethyl ether; hexane / 1 h / -78 °C 2: 88 percent / n-BuLi / tetrahydrofuran; hexane / 1.) room temperature, 1 h, 2.) -78 deg C to room temperature, 10 h 3: 90 percent / H2 / Ni(Ra) / ethyl acetate / 3 h / Ambient temperature 4: 100 percent / 10percent HCl / tetrahydrofuran; H2O / 16 h / 50 °C 5: 94 percent / oxalyl chloride, dimethyl sulfoxide, Et3N / CH2Cl2 / 1.) -60 deg C, 10 min, 2.) 15 min, 3.) warm to room temperature 6: 94 percent / n-BuLi / tetrahydrofuran; hexane / 1.) room temperature, 1 h, 2.) -78 deg C to room temperature, 10 h 7: NaHCO3, MCPBA / CH2Cl2 / 3 h / Ambient temperature 8: 90 percent / CuI / pentane; diethyl ether / 1.) 0 deg C, 15 min, 2.) 3 h 9: 98 percent / Li, NH3 / tetrahydrofuran / 1 h / Heating 10: 78 percent / sodium acetate, pyridinium chlorochromate / CH2Cl2 / 2 h 11: 89 percent / tetrahydrofuran / 0.5 h / 0 °C 12: 90 percent / sodium acetate, pyridinium chlorochromate / CH2Cl2 / 2 h 13: 33.8 percent / LDA, ZnCl2 / diethyl ether / 0 °C 14: H2 / palladium on carbon / ethanol / 3 h / Ambient temperature View Scheme

3-(methylthio)-1-propanol (505-10-2) + lasalocid (X 537 A) (25999-31-9) → 6-{7-[5-ethyl-5-(5-ethyl-5-hydroxy-6-methyl-tetrahydro-pyran-2-yl)-3-methyl-tetrahydro-furan-2-yl]-4-hydroxy-3,5-dimethyl-6-oxo-nonyl}-2-hydroxy-3-methyl-benzoic acid 3-methylsulfanyl-propyl ester

Conditions	Yield
With ethanol; dicyclohexyl-carbodiimide In diethyl ether for 5h; Heating;	84%

2-(hydroxymethyl)-12-crown-4 (75507-26-5) + lasalocid (X 537 A) (25999-31-9) → lasalocid ester with 2-(hydroxymethyl)-12-crown-4

Conditions	Yield
With dicyclohexyl-carbodiimide In diethyl ether for 5h; Heating;	82%

4-nitrobenzyl chloride (100-14-1) + lasalocid (X 537 A) (25999-31-9) → p-nitrobenzyl ester of lasalocid acid (1026999-92-7)

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene at 90℃; for 5h;	75%

morpholine (110-91-8) + lasalocid (X 537 A) (25999-31-9) → C38H63NO7 (1423441-54-6)

Conditions	Yield
With formaldehyd In toluene for 5h; Mannich Aminomethylation; Reflux;	75%

lasalocid (X 537 A) (25999-31-9) + diethylene glycol (111-46-6) → lasalocid 5-hydroxy-3-oxapentyl ester

Conditions	Yield
With dicyclohexyl-carbodiimide In diethyl ether for 0.5h; Heating;	74%

lasalocid (X 537 A) (25999-31-9) + 2,2'-[1,2-ethanediylbis(oxy)]bisethanol (112-27-6) → 8-hydroxy-3,6-dioxaoctyl lasaloic ester

Conditions	Yield
With dicyclohexyl-carbodiimide In diethyl ether for 0.5h; Heating;	71%

1 ,6-dibromohexane (629-03-8) + lasalocid (X 537 A) (25999-31-9) → C40H65BrO8

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene at 90℃; for 5h;	66%

C40H65BrO8 + lasalocid (X 537 A) (25999-31-9) → C74H118O16

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene at 90℃; for 5h;	60%

2-nitrobenzyl chloride (612-23-7) + lasalocid (X 537 A) (25999-31-9) → o-nitrobenzyl ester of lasalocid acid (1026999-90-5)

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene at 90℃; for 5h;	57%

2-bromomethylnaphthyl bromide (939-26-4) + lasalocid (X 537 A) (25999-31-9) → lasalocid 2-naphthylmethyl ester (1123683-88-4)

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene at 90℃; for 5h;	55%

lasalocid (X 537 A) (25999-31-9) + 3-Nitrobenzyl chloride (619-23-8) → m-nitrobenzyl ester of lasalocid acid (1026999-91-6)

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene at 90℃; for 5h;	47%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + lasalocid (X 537 A) (25999-31-9) → C38H57NO10

Conditions	Yield
With dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 20℃; for 24h; Inert atmosphere;	42%

C42H73BrO11 (1068438-03-8) + lasalocid (X 537 A) (25999-31-9) → C76H126O19

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene at 90℃; for 5h;	40%

lasalocid (X 537 A) (25999-31-9) → 4(R)-<5(S)-ethyl-3(S)-methyl-5-(5(R)-ethyl-5-hydroxy-6(S)-methyl-2(R)-tetrahydropyranyl)-2(S)-tetrahydrofuryl>hexan-3-one (31478-26-9, 87678-18-0) + 2-Hydroxy-3-methyl-6-((R)-3-methyl-4-oxo-butyl)-benzoic acid (73657-54-2)

Conditions	Yield
Product distribution; heat or base treatment;

methanol (67-56-1) + lasalocid (X 537 A) (25999-31-9) → 6-{(3R,4S,5S,7R)-7-[(2S,3S,5S)-5-Ethyl-5-((2R,5R,6S)-5-ethyl-5-hydroxy-6-methyl-tetrahydro-pyran-2-yl)-3-methyl-tetrahydro-furan-2-yl]-4-hydroxy-3,5-dimethyl-6-oxo-nonyl}-2-hydroxy-3-methyl-benzoic acid methyl ester (33855-15-1)

Conditions	Yield
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide at 25℃; for 48h;

N-BOC-1,2-diaminoethane (57260-73-8) + lasalocid (X 537 A) (25999-31-9) → [2-(6-{(3R,4S,5S,7R)-7-[(2S,3S,5S)-5-Ethyl-5-((2R,5R,6S)-5-ethyl-5-hydroxy-6-methyl-tetrahydro-pyran-2-yl)-3-methyl-tetrahydro-furan-2-yl]-4-hydroxy-3,5-dimethyl-6-oxo-nonyl}-2-hydroxy-3-methyl-benzoylamino)-ethyl]-carbamic acid tert-butyl ester (178912-24-8)

Conditions	Yield
With pyridine; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In N,N-dimethyl-formamide at 25℃; for 24h;

lasalocid (X 537 A) (25999-31-9) → N-(2-Amino-ethyl)-6-{(3R,4S,5S,7R)-7-[(2S,3S,5S)-5-ethyl-5-((2R,5R,6S)-5-ethyl-5-hydroxy-6-methyl-tetrahydro-pyran-2-yl)-3-methyl-tetrahydro-furan-2-yl]-4-hydroxy-3,5-dimethyl-6-oxo-nonyl}-2-hydroxy-3-methyl-benzamide (178912-25-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: EDC, HOBt, pyridine / dimethylformamide / 24 h / 25 °C 2: TFA / CH2Cl2 View Scheme

lasalocid (X 537 A) (25999-31-9) → C70H98N6O8

Conditions	Yield
Multi-step reaction with 3 steps 1: EDC, HOBt, pyridine / dimethylformamide / 24 h / 25 °C 2: TFA / CH2Cl2 3: EDC, HOBt, pyridine / dimethylformamide / 48 h / 25 °C View Scheme

lasalocid (X 537 A) (25999-31-9) → C76H105N7O8

Conditions	Yield
Multi-step reaction with 3 steps 1: EDC, HOBt, pyridine / dimethylformamide / 24 h / 25 °C 2: TFA / CH2Cl2 3: EDC, HOBt, pyridine / dimethylformamide / 48 h / 25 °C View Scheme

Upstream product

• 41733-86-2 lasalocid benzyl ester 
• 67045-68-5 3-methyl-6-(3(R)-formylbutyl)salicylic acid benzyl ester 
• 25999-20-6 lasalocid sodium 
• 73657-53-1 (2S)-2-<(2S,3S,5S)-5-ethyl-5-<(2R,5R,6S)-5-ethyl-5-hydroxy-6-methyltetrahydropyran-2-yl>-3-methyltetrahydrofur-2-yl>butan-1-ol 
• 84911-92-2 (3RS,4S)-4-<(2S,3S,5S)-5-ethyl-5-<(2R,5R,6S)-5-ethyl-5-hydroxy-6-methyltetrahydropyran-2-yl>-3-methyltetrahydrofur-2-yl>hexan-3-ol 
• 84911-91-1 (2R)-2-<(2S,3S,5S)-5-ethyl-5-<(2R,5R,6S)-5-ethyl-5-hydroxy-6-methyltetrahydropyran-2-yl>-3-methyltetrahydrofur-2-yl>butanal 
• 31478-26-9 4(R)-<5(S)-ethyl-3(S)-methyl-5-(5(R)-ethyl-5-hydroxy-6(S)-methyl-2(R)-tetrahydropyranyl)-2(S)-tetrahydrofuryl>hexan-3-one 
• 75371-81-2 3-methyl-6-(3(R)-methyl-4,5-O-isopropylidenepentyl)salicylic acid methyl ester 
• 73657-51-9 benzyl 2(S)-<5(S)-ethyl-3(S)-methyl-5-(5(R)-ethyl-5-hydroxy-6(S)-methyl-2(R)-tetrahydropyranyl)-2(S)-tetrahydrofuryl>butyl ether 
• 73657-52-0 benzyl 2(S)-<5(S)-ethyl-3(S)-methyl-5-(3(R)-1,5-dioxo-4(S)-methylspiro<2.5>-6(R)-octyl)-2(S)-tetrahydrofuryl>butyl ether 
• 75371-80-1 2-(dibenzylamino)-3-methyl-6-(3(R)-methyl-4-pentenyl)benzoic acid methyl ester 
• 84985-06-8 benzyl 2(S)-<5(S)-carbomethoxy-3(S)-methyl-5-(5,6-dihydro)-5(S)-(methoxymethylenoxy)-6(S)-methyl-2(R)-pyranyl-2(S)-tetrahydrofuryl>butyl ether 
• 75371-88-9 3-methyl-6-(3(R)-methyl-4,5-dihydroxypentyl)salicylic acid methyl ester 
• 84911-36-4 2(S)-<5(S)-ethyl-3(S)-methyl-5-(5(R)-ethyl-5-(trimethylsiloxy)-6(S)-methyl-2(R)-tetrahydropyranyl)-2(S)-tetrahydrofuryl>butan-1-ol 

Downstream Products

• 31478-26-9 4(R)-<5(S)-ethyl-3(S)-methyl-5-(5(R)-ethyl-5-hydroxy-6(S)-methyl-2(R)-tetrahydropyranyl)-2(S)-tetrahydrofuryl>hexan-3-one 
• 73657-54-2 2-Hydroxy-3-methyl-6-((R)-3-methyl-4-oxo-butyl)-benzoic acid 
• 33855-15-1 6-{(3R,4S,5S,7R)-7-[(2S,3S,5S)-5-Ethyl-5-((2R,5R,6S)-5-ethyl-5-hydroxy-6-methyl-tetrahydro-pyran-2-yl)-3-methyl-tetrahydro-furan-2-yl]-4-hydroxy-3,5-dimethyl-6-oxo-nonyl}-2-hydroxy-3-methyl-benzoic acid methyl ester 
• 178912-24-8 [2-(6-{(3R,4S,5S,7R)-7-[(2S,3S,5S)-5-Ethyl-5-((2R,5R,6S)-5-ethyl-5-hydroxy-6-methyl-tetrahydro-pyran-2-yl)-3-methyl-tetrahydro-furan-2-yl]-4-hydroxy-3,5-dimethyl-6-oxo-nonyl}-2-hydroxy-3-methyl-benzoylamino)-ethyl]-carbamic acid tert-butyl ester 
• 178912-25-9 N-(2-Amino-ethyl)-6-{(3R,4S,5S,7R)-7-[(2S,3S,5S)-5-ethyl-5-((2R,5R,6S)-5-ethyl-5-hydroxy-6-methyl-tetrahydro-pyran-2-yl)-3-methyl-tetrahydro-furan-2-yl]-4-hydroxy-3,5-dimethyl-6-oxo-nonyl}-2-hydroxy-3-methyl-benzamide 
• 1026999-92-7 p-nitrobenzyl ester of lasalocid acid 
• 1026999-90-5 o-nitrobenzyl ester of lasalocid acid 
• 1026999-91-6 m-nitrobenzyl ester of lasalocid acid 
• 1123683-88-4 lasalocid 2-naphthylmethyl ester 
• 1097648-84-4 lasalocid 1-naphthylmethyl ester 
• 103882-72-0 C₆H₇N*C₃₄H₅₄O₈ 
• 1423441-54-6 C₃₈H₆₃NO₇ 

Relevant articles and documents

Lasalocid acid as a lipophilic carrier ionophore for allylamine: Spectroscopic, crystallographic and microbiological investigation

A new complex of lasalocid acid with allylamine (LAS-AM) is synthesised and studied by X-ray, FT-IR, 1H NMR and 13C NMR, ESI MS methods. In the solid state allylamine is protonated and all protons of NH3+ are hy

X-ray crystallographic, FT-IR and NMR studies as well as anticancer and antibacterial activity of the salt formed between ionophore antibiotic Lasalocid acid and amines

Two new complexes of the ionophore antibiotic Lasalocid acid (LAS) with phenylamine (PhA) and butylamine (BuA) were synthesized and their molecular structures were studied using single crystal X-ray diffraction and spectroscopic methods. In the solid state both amines are protonated and all NH3+ protons are hydrogen bonded to etheric, hydroxyl and carboxylic oxygen atoms of the LAS anion. In chloroform solutions the structure observed in the crystal of LAS-BuA complex is preserved and an equilibrium between the LAS-PhA complex and dissociated Lasalocid acid and phenylamine is observed. In vitro antimicrobial tests of the complexes showed a significant activity towards some strains of Gram-positive bacteria. For the first time Lasalocid acid and its complexes with amines were tested in vitro for cytotoxic activity against human cancer cell lines: A-549 (lung), MCF-7 (breast), HT-29 (colon) and mouse cancer cell line P-388 (leukemia). We found that LAS and its complexes are strong cytotoxic agents towards all tested cell lines. The cytostatic activity of the compounds studied is greater than that of cisplatin, indicating that Lasalocid and its complexes are promising candidates for new anticancer drugs.

Structural and spectroscopic studies of a new 2-naphthylmethyl ester of lasalocid acid

A new lasalocid 2-naphthylmethyl ester (NAFB) has been synthesised and studied by X-ray, 1H NMR, 13C NMR, FT-IR, UV-vis, fluorescence-spectroscopy as well as by the PM5 semiempirical method. The crystals of NAFB are monoclinic, space