Lasalocid supplier | CasNO.25999-31-9

Name
Lasalocid
EINECS 247-401-9
CAS No. 25999-31-9
Article Data10
CAS DataBase
Density 1.119g/cm³
Solubility
Melting Point 110-114°; mp 100-109° (unsharp)
Formula C34H54 O8
Boiling Point 735.7°Cat760mmHg
Molecular Weight 590.798
Flash Point 224.8°C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 2,3-Cresoticacid,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]-,(-)- (8CI);Benzoic acid, 6-[7-[5-ethyl-5-(5-ethyltetrahydro-5-hydroxy-6-methyl-2H-pyran-2-yl)tetrahydro-3-methyl-2-furanyl]-4-hydroxy-3,5-dimethyl-6-oxononyl]-2-hydroxy-3-methyl-,[2R-[2a[2S*(3R*,4S*,5S*,7R*),3S*,5S*],5a,6b]]-;Antibiotic X 537A;Ionophore X 537A;Lasalocid;Lasalocid A;Lasalocide A;X 537A;
PSA 133.52000
LogP 5.84220

Synthetic route

: 41733-86-2
lasalocid benzyl ester

: 25999-31-9
lasalocid (X 537 A)

Conditions

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

: 67045-68-5
3-methyl-6-(3(R)-formylbutyl)salicylic acid benzyl ester

: 25999-31-9
lasalocid (X 537 A)

Conditions

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

: 25999-20-6
lasalocid sodium

: 25999-31-9
lasalocid (X 537 A)

Conditions

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

: 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

: 25999-31-9
lasalocid (X 537 A)

Conditions

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

: 84911-92-2, 84985-23-9, 87678-43-1, 87678-51-1
(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

: 25999-31-9
lasalocid (X 537 A)

Conditions

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

: 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

: 25999-31-9
lasalocid (X 537 A)

Conditions

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

: 31478-26-9, 87678-18-0
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

: 25999-31-9
lasalocid (X 537 A)

Conditions

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

: 75371-81-2, 84911-50-2, 84911-98-8
3-methyl-6-(3(R)-methyl-4,5-O-isopropylidenepentyl)salicylic acid methyl ester

: 25999-31-9
lasalocid (X 537 A)

Conditions

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

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

: 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

: 25999-31-9
lasalocid (X 537 A)

Conditions

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

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

: 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

: 25999-31-9
lasalocid (X 537 A)

Conditions

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

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

: 75371-80-1
2-(dibenzylamino)-3-methyl-6-(3(R)-methyl-4-pentenyl)benzoic acid methyl ester

: 25999-31-9
lasalocid (X 537 A)

Conditions

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

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

: 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

: 25999-31-9
lasalocid (X 537 A)

Conditions

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

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

: 75371-88-9, 84911-49-9, 84911-97-7
3-methyl-6-(3(R)-methyl-4,5-dihydroxypentyl)salicylic acid methyl ester

: 25999-31-9
lasalocid (X 537 A)

Conditions

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

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

: 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

: 25999-31-9
lasalocid (X 537 A)

Conditions

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

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

: 75371-87-8, 84911-48-8, 84911-96-6
2-amino-3-methyl-6-(3(R)-methyl-4,5-O-isopropylidenepentyl)benzoic acid methyl ester

: 25999-31-9
lasalocid (X 537 A)

Conditions

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

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

: 84911-38-6
(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

: 25999-31-9
lasalocid (X 537 A)

Conditions

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

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

: 25999-31-9
lasalocid (X 537 A)

Conditions

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

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

: 84911-35-3
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

: 25999-31-9
lasalocid (X 537 A)

Conditions

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

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

: 75371-89-0, 84911-51-3, 84911-99-9
2-(β-methoxyethoxymethyl)-3-methyl-6-(3(R)-methyl-4,5-O-isopropylidenepentyl)salicylic acid methyl ester

: 25999-31-9
lasalocid (X 537 A)

Conditions

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

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

: 84911-52-4, 84912-00-5
2-(β-methoxyethoxymethyl)-3-methyl-6-(3(R)-methyl-4,5-O-isopropylidenepentyl)salicylic acid benzyl ester

: 25999-31-9
lasalocid (X 537 A)

Conditions

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

: 75371-86-7, 84911-47-7, 84911-95-5
2-(dibenzylamino)-3-methyl-6-(3(R)-methyl-4,5-O-isopropylidenepentyl)benzoic acid methyl ester

: 25999-31-9
lasalocid (X 537 A)

Conditions

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

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

: 84911-90-0
benzyl 2(S)-<5(S)-ethyl-3(S)-methyl-5-(6(S)-methyl-5-methylene-2(R)-tetrahydropyranyl)-2(S)-tetrahydrofuryl>butyl ether

: 25999-31-9
lasalocid (X 537 A)

Conditions

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

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

: 84911-37-5
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

: 25999-31-9
lasalocid (X 537 A)

Conditions

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

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

: 84911-89-7, 87678-36-2
benzyl 2(S)-<5(S)-ethyl-3(S)-methyl-5-(6(S)-methyl-5-oxo-2(R)-tetrahydropyranyl)-2(S)-tetrahydrofuryl>butyl ether

: 25999-31-9
lasalocid (X 537 A)

Conditions

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

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

: 75371-90-3, 84911-53-5, 84912-01-6, 87598-86-5, 87599-04-0
3-methyl-6-(3(R)-methyl-4,5-dihydroxypentyl)salicylic acid benzyl ester

: 25999-31-9
lasalocid (X 537 A)

Conditions

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

: 84985-18-2
benzyl 2(S)-<5(S)-ethyl-3(S)-methyl-5-(5(S)-(methoxymethylenoxy)-6(S)-methyl-2(R)-tetrahydropyranyl)-2(S)-tetrahydrofuryl>butyl ether

: 25999-31-9
lasalocid (X 537 A)

Conditions

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

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

: 84911-87-5, 84985-13-7, 84985-14-8, 84985-15-9, 87678-33-9
benzyl 2(S)-<5(R)-vinyl-3(S)-methyl-5-(5(S)-(methoxymethylenoxy)-6(S)-methyl-2(R)-tetrahydropyranyl)-2(S)-tetrahydrofuryl>butyl ether

: 25999-31-9
lasalocid (X 537 A)

Conditions

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

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

: 84985-12-6
benzyl 2(S)-<5(S)-formyl-3(S)-methyl-5-(5(S)-(methoxymethylenoxy)-6(S)-methyl-2(R)-tetrahydropyranyl)-2(S)-tetrahydrofuryl>butyl ether

: 25999-31-9
lasalocid (X 537 A)

Conditions

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

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

: 84985-09-1
benzyl 2(S)-<5(S)-carbomethoxy-3(S)-methyl-5-(5(S)-(methoxymethylenoxy)-6(S)-methyl-2(R)-tetrahydropyranyl)-2(S)-tetrahydrofuryl>butyl ether

: 25999-31-9
lasalocid (X 537 A)

Conditions

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

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

: 505-10-2
3-(methylthio)-1-propanol

: 25999-31-9
lasalocid (X 537 A)

: 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

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

: 75507-26-5
2-(hydroxymethyl)-12-crown-4

: 25999-31-9
lasalocid (X 537 A)

: lasalocid ester with 2-(hydroxymethyl)-12-crown-4

Conditions

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

: 100-14-1
4-nitrobenzyl chloride

: 25999-31-9
lasalocid (X 537 A)

: 1026999-92-7
p-nitrobenzyl ester of lasalocid acid

Conditions

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

: 110-91-8
morpholine

: 25999-31-9
lasalocid (X 537 A)

: 1423441-54-6
C38H63NO7

Conditions

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

: 25999-31-9
lasalocid (X 537 A)

: 111-46-6
diethylene glycol

: lasalocid 5-hydroxy-3-oxapentyl ester

Conditions

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

: 25999-31-9
lasalocid (X 537 A)

: 112-27-6
2,2'-[1,2-ethanediylbis(oxy)]bisethanol

: 8-hydroxy-3,6-dioxaoctyl lasaloic ester

Conditions

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

: 629-03-8
1 ,6-dibromohexane

: 25999-31-9
lasalocid (X 537 A)

: C40H65BrO8

Conditions

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

: C40H65BrO8

: 25999-31-9
lasalocid (X 537 A)

: C74H118O16

Conditions

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

: 612-23-7
2-nitrobenzyl chloride

: 25999-31-9
lasalocid (X 537 A)

: 1026999-90-5
o-nitrobenzyl ester of lasalocid acid

Conditions

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

: 939-26-4
2-bromomethylnaphthyl bromide

: 25999-31-9
lasalocid (X 537 A)

: 1123683-88-4
lasalocid 2-naphthylmethyl ester

Conditions

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

: 25999-31-9
lasalocid (X 537 A)

: 619-23-8
3-Nitrobenzyl chloride

: 1026999-91-6
m-nitrobenzyl ester of lasalocid acid

Conditions

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

: 6066-82-6
1-hydroxy-pyrrolidine-2,5-dione

: 25999-31-9
lasalocid (X 537 A)

: C38H57NO10

Conditions

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

: 1068438-03-8
C42H73BrO11

: 25999-31-9
lasalocid (X 537 A)

: C76H126O19

Conditions

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

: 25999-31-9
lasalocid (X 537 A)

A: 31478-26-9, 87678-18-0
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

B: 73657-54-2
2-Hydroxy-3-methyl-6-((R)-3-methyl-4-oxo-butyl)-benzoic acid

Conditions

Conditions	Yield
Product distribution; heat or base treatment;

: 67-56-1
methanol

: 25999-31-9
lasalocid (X 537 A)

: 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

Conditions

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

: 57260-73-8
N-BOC-1,2-diaminoethane

: 25999-31-9
lasalocid (X 537 A)

: 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

Conditions

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

: 25999-31-9
lasalocid (X 537 A)

: 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

Conditions

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

: 25999-31-9
lasalocid (X 537 A)

: C70H98N6O8

Conditions

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

: 25999-31-9
lasalocid (X 537 A)

: C76H105N7O8

Conditions

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 Chemical Properties

IUPAC Name: 6-[(3R,4S,5S,7R)-7-[(2S,3S,5S)-5-Ethyl-5-[(2R,5R,6S)-5-ethyl-5-hydroxy-6-methyloxan-2-yl]-3-methyloxolan-2-yl]-4-hydroxy-3,5-dimethyl-6-oxononyl]-2-hydroxy-3-methylbenzoic acid
Molecular Formula: C₃₄H₅₄O₈
Molecular Weight: 590.78776g/mol
Freely Rotating Bonds: 16
Polar Surface Area: 89.52 Å²
Index of Refraction: 1.528
Molar Refractivity: 162.72 cm³
Molar Volume: 527.7 cm³
Polarizability: 64.5 ×10^-24cm³
Surface Tension: 43.6 dyne/cm
Density: 1.119 g/cm³
Flash Point: 224.8 °C
Enthalpy of Vaporization: 112.66 kJ/mol
Boiling Point: 735.7 °C at 760 mmHg
Vapour Pressure: 1.01E-22 mmHg at 25°C
The Cas Register Number of Lasalocid is 25999-31-9 .The chemical synonyms of Lasalocid (CAS No.25999-31-9) are 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 .The molecular structure of Lasalocid (CAS No.25999-31-9) is.

Lasalocid Uses

It can be used as drugs, feed additives.

Lasalocid Toxicity Data With Reference

1.	skn-rbt 100 mg/24H MLD	DCTODJ Drug and Chemical Toxicology. 8 (1985),451.
2.	eye-rbt 50 mg MOD	DCTODJ Drug and Chemical Toxicology. 8 (1985),451.
3.	ipr-rat LD50:8 mg/kg	DCTODJ Drug and Chemical Toxicology. 8 (1985),451.
4.	orl-hor LD50:22 mg/kg	AJVRAH American Journal of Veterinary Research. 42 (1981),456.

Lasalocid Safety Profile

Poison by ingestion and intraperitoneal routes. An eye and skin irritant. When heated to decomposition it emits acrid smoke and irritating fumes.

Product Name

Lasalocid

Synthetic route

Lasalocid Chemical Properties

Lasalocid Uses

Lasalocid Toxicity Data With Reference

Lasalocid Safety Profile

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