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104987-11-3

Basic Information
CAS No.: 104987-11-3
Name: Tacrolimus
Molecular Structure:
Molecular Structure of 104987-11-3 (Tacrolimus)
Formula: C44H69NO12
Molecular Weight: 804.02
Synonyms: 4,5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-heptadecahydro-5,19-dihydroxy-3-;FK-506;FK506;15,19-Epoxy-3H-pyrido[2,1-c][1,4]oxaazacyclotricosine- 1,7,20,21(4H,23H)-tetrone,5,6,8,11,- 12,13,14,15,16,17,18,19,24,25,26,26ahexadecahydro- 5,19-dihydroxy-3-[(1E)-2- [(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]- 1-methylethenyl]-14,16-dimethoxy-4,10,12,18- tetramethyl-8-(2-propenyl)-,(3S,4R,5S,8R,- 9E,12S,14S,15R,16S,18R,19R,26aS)-;FR 900506;Prograf;dimethoxy-4,10,12,18-tetramethyl-8-(2-propenyl)-,(3S,4R,5S,8R,12S,14S,15R,16S,18R,19R,26aS)-;FK 506;Fujimycin;FR-900506;[(E)-2-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-1-methylethenyl]-14,16-;Tacrolimus (FK506);Tacrolimus(FK-506);Tacrolimus(FK506);Tacrolimus, FK-506;Taccrolimus;Tacrolimus [GMP];15,19-epoxy-3H-pyrido[2,1-c][1,4]oxaazacyclotricosine-1,7,20,21(23H)-tetrone,;Prograde metamorphismPrograf;
EINECS: 1308068-626-2
Density: 1.19 g/cm3
Melting Point: 113-115 °C
Boiling Point: 871.7 °C at 760 mmHg
Flash Point: 481 °C
Solubility: DMSO: >3 mg/mL
Appearance: White or off-white crystalline powder
Hazard Symbols: ToxicT,IrritantXi
Risk Codes: 25-36/37/38
Safety: 45-36-26
Transport Information: UN 2811 6.1/PG 3
PSA: 178.36000
LogP: 4.57690
Synthetic route
118977-96-1

C56H97NO12Si2

104987-11-3

Tacrolimus

Conditions
ConditionsYield
With hydrogen fluoride In acetonitrile at 20℃; for 0.05h;100%
With hydrogen fluoride; acetonitrile In dichloromethane at 0℃; for 0.0833333h;81%
With hydrogen fluoride In acetonitrile at 20℃;81%
133941-75-0

24,33-Bis-(t.butyl-dimethylsilyl)-FK 506

104987-11-3

Tacrolimus

Conditions
ConditionsYield
With hydrogen fluoride In acetonitrile at 50℃; for 0.2h;100%
With hydrogen fluoride In acetonitrile at 20℃; for 2.5h;
128685-18-7

14-<(tert-butyldimethylsilyl)oxy>-24,32-bis<(triisopropylsilyl)oxy>-FK506

104987-11-3

Tacrolimus

Conditions
ConditionsYield
With hydrogen fluoride In acetonitrile for 18h; Ambient temperature;73%
176656-40-9

C66H101NO11Si2

104987-11-3

Tacrolimus

Conditions
ConditionsYield
With hydrogen fluoride; 3,3-dimethyldioxirane 1) acetone, CH2Cl2, -45 deg C -> -25 deg C, 1 h; -25 deg C -> 0 deg C, 1 h, 2) MeCN, 6 h; Yield given. Multistep reaction;
197250-11-6

C66H101NO12Si2

104987-11-3

Tacrolimus

Conditions
ConditionsYield
With hydrogen fluoride In acetonitrile at 20℃; for 10h; Cyclization; desilylation;10.5 mg

C55H95NO13Si2

104987-11-3

Tacrolimus

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 46 percent / epichlorohydrin / 1,2-dichloro-benzene / 0.05 h / 140 °C
2: 100 percent / aq. HF / acetonitrile / 0.2 h / 50 °C
View Scheme

{1-hydroxy-23,25-dimethoxy-12-[2-(3-methoxy-4-triethylsilanyloxy-cyclohexyl)-1-methyl-vinyl]-13,19,21,27-tetramethyl-2,3,10,16-tetraoxo-14-triethylsilanyloxy-11,28-dioxa-4-aza-tricyclo[22.3.1.04,9]octacos-18-en-17-yl}-acetaldehyde

104987-11-3

Tacrolimus

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 43 percent / epichlorohydrin / 1,2-dichloro-benzene / 0.05 h / 140 °C
2: 100 percent / aq. HF / acetonitrile / 0.05 h / 20 °C
View Scheme
197250-10-5

C69H107NO12Si2

104987-11-3

Tacrolimus

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 100 percent / dimethyl dioxirane / acetone / 2.17 h / -50 - -26 °C
2: 10.5 mg / aq. HF / acetonitrile / 10 h / 20 °C
View Scheme

C72H112INO13Si2

104987-11-3

Tacrolimus

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 110 percent / C8K-ZnCl2-AgOAc / tetrahydrofuran / 1 h / 0 °C
2: 100 percent / dimethyl dioxirane / acetone / 2.17 h / -50 - -26 °C
3: 10.5 mg / aq. HF / acetonitrile / 10 h / 20 °C
View Scheme

C72H113NO14Si2

104987-11-3

Tacrolimus

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 88 percent / triphenylphosphine; imidazole; iodine / toluene / 0.5 h / 70 °C
2: 110 percent / C8K-ZnCl2-AgOAc / tetrahydrofuran / 1 h / 0 °C
3: 100 percent / dimethyl dioxirane / acetone / 2.17 h / -50 - -26 °C
4: 10.5 mg / aq. HF / acetonitrile / 10 h / 20 °C
View Scheme

C80H121NO15Si2

104987-11-3

Tacrolimus

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 92 percent / DDQ / CH2Cl2; H2O / 0.83 h / 20 °C
2: 88 percent / triphenylphosphine; imidazole; iodine / toluene / 0.5 h / 70 °C
3: 110 percent / C8K-ZnCl2-AgOAc / tetrahydrofuran / 1 h / 0 °C
4: 100 percent / dimethyl dioxirane / acetone / 2.17 h / -50 - -26 °C
5: 10.5 mg / aq. HF / acetonitrile / 10 h / 20 °C
View Scheme

C80H123NO16Si2

104987-11-3

Tacrolimus

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 21.0 mg / Et3N; methyl-2-chloropyridinium iodide / CH2Cl2 / 14 h / 20 °C
2: 92 percent / DDQ / CH2Cl2; H2O / 0.83 h / 20 °C
3: 88 percent / triphenylphosphine; imidazole; iodine / toluene / 0.5 h / 70 °C
4: 110 percent / C8K-ZnCl2-AgOAc / tetrahydrofuran / 1 h / 0 °C
5: 100 percent / dimethyl dioxirane / acetone / 2.17 h / -50 - -26 °C
6: 10.5 mg / aq. HF / acetonitrile / 10 h / 20 °C
View Scheme

C63H93NO13Si

104987-11-3

Tacrolimus

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 81 percent / Dess-Martin periodinane / CH2Cl2 / 3 h / Ambient temperature
2: 84 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
3: 83 percent / I2, PPh3, imidazole / toluene / 0.5 h / 75 °C
4: 74 percent / 1) KHMDS / tetrahydrofuran; toluene / 1) -78 deg C, 30 min, 2) 30 min
5: 67 percent / graphite, potassium, ZnCl2, AgOAc / tetrahydrofuran / 1.5 h / Ambient temperature
6: 1) dimethyldioxirane, 2) 40percent HF / 1) acetone, CH2Cl2, -45 deg C -> -25 deg C, 1 h; -25 deg C -> 0 deg C, 1 h, 2) MeCN, 6 h
View Scheme

C63H92INO12Si

104987-11-3

Tacrolimus

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 74 percent / 1) KHMDS / tetrahydrofuran; toluene / 1) -78 deg C, 30 min, 2) 30 min
2: 67 percent / graphite, potassium, ZnCl2, AgOAc / tetrahydrofuran / 1.5 h / Ambient temperature
3: 1) dimethyldioxirane, 2) 40percent HF / 1) acetone, CH2Cl2, -45 deg C -> -25 deg C, 1 h; -25 deg C -> 0 deg C, 1 h, 2) MeCN, 6 h
View Scheme

C63H93NO13Si

104987-11-3

Tacrolimus

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 83 percent / I2, PPh3, imidazole / toluene / 0.5 h / 75 °C
2: 74 percent / 1) KHMDS / tetrahydrofuran; toluene / 1) -78 deg C, 30 min, 2) 30 min
3: 67 percent / graphite, potassium, ZnCl2, AgOAc / tetrahydrofuran / 1.5 h / Ambient temperature
4: 1) dimethyldioxirane, 2) 40percent HF / 1) acetone, CH2Cl2, -45 deg C -> -25 deg C, 1 h; -25 deg C -> 0 deg C, 1 h, 2) MeCN, 6 h
View Scheme

C63H93NO14Si

104987-11-3

Tacrolimus

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 47.3 mg / 2-chloro-1-methylpyridinium iodide, NET3 / CH2Cl2 / 6 h / Heating
2: 84 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
3: 83 percent / I2, PPh3, imidazole / toluene / 0.5 h / 75 °C
4: 74 percent / 1) KHMDS / tetrahydrofuran; toluene / 1) -78 deg C, 30 min, 2) 30 min
5: 67 percent / graphite, potassium, ZnCl2, AgOAc / tetrahydrofuran / 1.5 h / Ambient temperature
6: 1) dimethyldioxirane, 2) 40percent HF / 1) acetone, CH2Cl2, -45 deg C -> -25 deg C, 1 h; -25 deg C -> 0 deg C, 1 h, 2) MeCN, 6 h
View Scheme

C63H95NO14Si

104987-11-3

Tacrolimus

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 1) 2-chloro-1-methylpyridinium iodide, NEt3, 2) NEt3 / 1) CH2Cl2, reflux, 17 h, 2) EtOH, 5 h
2: 81 percent / Dess-Martin periodinane / CH2Cl2 / 3 h / Ambient temperature
3: 84 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
4: 83 percent / I2, PPh3, imidazole / toluene / 0.5 h / 75 °C
5: 74 percent / 1) KHMDS / tetrahydrofuran; toluene / 1) -78 deg C, 30 min, 2) 30 min
6: 67 percent / graphite, potassium, ZnCl2, AgOAc / tetrahydrofuran / 1.5 h / Ambient temperature
7: 1) dimethyldioxirane, 2) 40percent HF / 1) acetone, CH2Cl2, -45 deg C -> -25 deg C, 1 h; -25 deg C -> 0 deg C, 1 h, 2) MeCN, 6 h
View Scheme

C63H91NO13Si

104987-11-3

Tacrolimus

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 84 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
2: 83 percent / I2, PPh3, imidazole / toluene / 0.5 h / 75 °C
3: 74 percent / 1) KHMDS / tetrahydrofuran; toluene / 1) -78 deg C, 30 min, 2) 30 min
4: 67 percent / graphite, potassium, ZnCl2, AgOAc / tetrahydrofuran / 1.5 h / Ambient temperature
5: 1) dimethyldioxirane, 2) 40percent HF / 1) acetone, CH2Cl2, -45 deg C -> -25 deg C, 1 h; -25 deg C -> 0 deg C, 1 h, 2) MeCN, 6 h
View Scheme

C68H105NO15Si

104987-11-3

Tacrolimus

Conditions
ConditionsYield
Multi-step reaction with 12 steps
1: NaHCO3, KBr, 4-methoxy-2,2,6,6-tetramethylpiperidinyloxy free radical, NaOCl / CH2Cl2 / 1.33 h / 0 °C
2: NaH2PO4, NaClO2 / 2-methyl-propan-2-ol; H2O; various solvent(s) / 2 h
3: 495 mg / diethyl ether
4: Dess-Martin periodinane / CH2Cl2 / 1 h
5: LiOH*H2O / tetrahydrofuran / 0.5 h
6: 1) TESOTf, 2,6-lutidine, 2) TBAF, AcOH / 1) CH2Cl2, 0 deg C, 1h, 2) THF, 0 deg C, 1 h
7: 47.3 mg / 2-chloro-1-methylpyridinium iodide, NET3 / CH2Cl2 / 6 h / Heating
8: 84 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
9: 83 percent / I2, PPh3, imidazole / toluene / 0.5 h / 75 °C
10: 74 percent / 1) KHMDS / tetrahydrofuran; toluene / 1) -78 deg C, 30 min, 2) 30 min
11: 67 percent / graphite, potassium, ZnCl2, AgOAc / tetrahydrofuran / 1.5 h / Ambient temperature
12: 1) dimethyldioxirane, 2) 40percent HF / 1) acetone, CH2Cl2, -45 deg C -> -25 deg C, 1 h; -25 deg C -> 0 deg C, 1 h, 2) MeCN, 6 h
View Scheme
Multi-step reaction with 10 steps
1: NaHCO3, KBr, 4-methoxy-2,2,6,6-tetramethylpiperidinyloxy free radical, NaOCl / CH2Cl2 / 1.33 h / 0 °C
2: NaH2PO4, NaClO2 / 2-methyl-propan-2-ol; H2O; various solvent(s) / 2 h
3: 1) TESOTf, 2,6-lutidine, 2) TBAF, AcOH / 1) CH2Cl2, 0 deg C, 1 h, 2) THF, 0 deg C, 1 h
4: 1) 2-chloro-1-methylpyridinium iodide, NEt3, 2) NEt3 / 1) CH2Cl2, reflux, 17 h, 2) EtOH, 5 h
5: 81 percent / Dess-Martin periodinane / CH2Cl2 / 3 h / Ambient temperature
6: 84 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
7: 83 percent / I2, PPh3, imidazole / toluene / 0.5 h / 75 °C
8: 74 percent / 1) KHMDS / tetrahydrofuran; toluene / 1) -78 deg C, 30 min, 2) 30 min
9: 67 percent / graphite, potassium, ZnCl2, AgOAc / tetrahydrofuran / 1.5 h / Ambient temperature
10: 1) dimethyldioxirane, 2) 40percent HF / 1) acetone, CH2Cl2, -45 deg C -> -25 deg C, 1 h; -25 deg C -> 0 deg C, 1 h, 2) MeCN, 6 h
View Scheme

C69H106INO12Si2

104987-11-3

Tacrolimus

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 67 percent / graphite, potassium, ZnCl2, AgOAc / tetrahydrofuran / 1.5 h / Ambient temperature
2: 1) dimethyldioxirane, 2) 40percent HF / 1) acetone, CH2Cl2, -45 deg C -> -25 deg C, 1 h; -25 deg C -> 0 deg C, 1 h, 2) MeCN, 6 h
View Scheme

C68H103NO15Si

104987-11-3

Tacrolimus

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1: NaH2PO4, NaClO2 / 2-methyl-propan-2-ol; H2O; various solvent(s) / 2 h
2: 495 mg / diethyl ether
3: Dess-Martin periodinane / CH2Cl2 / 1 h
4: LiOH*H2O / tetrahydrofuran / 0.5 h
5: 1) TESOTf, 2,6-lutidine, 2) TBAF, AcOH / 1) CH2Cl2, 0 deg C, 1h, 2) THF, 0 deg C, 1 h
6: 47.3 mg / 2-chloro-1-methylpyridinium iodide, NET3 / CH2Cl2 / 6 h / Heating
7: 84 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
8: 83 percent / I2, PPh3, imidazole / toluene / 0.5 h / 75 °C
9: 74 percent / 1) KHMDS / tetrahydrofuran; toluene / 1) -78 deg C, 30 min, 2) 30 min
10: 67 percent / graphite, potassium, ZnCl2, AgOAc / tetrahydrofuran / 1.5 h / Ambient temperature
11: 1) dimethyldioxirane, 2) 40percent HF / 1) acetone, CH2Cl2, -45 deg C -> -25 deg C, 1 h; -25 deg C -> 0 deg C, 1 h, 2) MeCN, 6 h
View Scheme
Multi-step reaction with 9 steps
1: NaH2PO4, NaClO2 / 2-methyl-propan-2-ol; H2O; various solvent(s) / 2 h
2: 1) TESOTf, 2,6-lutidine, 2) TBAF, AcOH / 1) CH2Cl2, 0 deg C, 1 h, 2) THF, 0 deg C, 1 h
3: 1) 2-chloro-1-methylpyridinium iodide, NEt3, 2) NEt3 / 1) CH2Cl2, reflux, 17 h, 2) EtOH, 5 h
4: 81 percent / Dess-Martin periodinane / CH2Cl2 / 3 h / Ambient temperature
5: 84 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
6: 83 percent / I2, PPh3, imidazole / toluene / 0.5 h / 75 °C
7: 74 percent / 1) KHMDS / tetrahydrofuran; toluene / 1) -78 deg C, 30 min, 2) 30 min
8: 67 percent / graphite, potassium, ZnCl2, AgOAc / tetrahydrofuran / 1.5 h / Ambient temperature
9: 1) dimethyldioxirane, 2) 40percent HF / 1) acetone, CH2Cl2, -45 deg C -> -25 deg C, 1 h; -25 deg C -> 0 deg C, 1 h, 2) MeCN, 6 h
View Scheme

C68H101NO16Si

104987-11-3

Tacrolimus

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 1) TESOTf, 2,6-lutidine, 2) TBAF, AcOH / 1) CH2Cl2, 0 deg C, 1h, 2) THF, 0 deg C, 1 h
2: 47.3 mg / 2-chloro-1-methylpyridinium iodide, NET3 / CH2Cl2 / 6 h / Heating
3: 84 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
4: 83 percent / I2, PPh3, imidazole / toluene / 0.5 h / 75 °C
5: 74 percent / 1) KHMDS / tetrahydrofuran; toluene / 1) -78 deg C, 30 min, 2) 30 min
6: 67 percent / graphite, potassium, ZnCl2, AgOAc / tetrahydrofuran / 1.5 h / Ambient temperature
7: 1) dimethyldioxirane, 2) 40percent HF / 1) acetone, CH2Cl2, -45 deg C -> -25 deg C, 1 h; -25 deg C -> 0 deg C, 1 h, 2) MeCN, 6 h
View Scheme

C68H103NO16Si

104987-11-3

Tacrolimus

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: 495 mg / diethyl ether
2: Dess-Martin periodinane / CH2Cl2 / 1 h
3: LiOH*H2O / tetrahydrofuran / 0.5 h
4: 1) TESOTf, 2,6-lutidine, 2) TBAF, AcOH / 1) CH2Cl2, 0 deg C, 1h, 2) THF, 0 deg C, 1 h
5: 47.3 mg / 2-chloro-1-methylpyridinium iodide, NET3 / CH2Cl2 / 6 h / Heating
6: 84 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
7: 83 percent / I2, PPh3, imidazole / toluene / 0.5 h / 75 °C
8: 74 percent / 1) KHMDS / tetrahydrofuran; toluene / 1) -78 deg C, 30 min, 2) 30 min
9: 67 percent / graphite, potassium, ZnCl2, AgOAc / tetrahydrofuran / 1.5 h / Ambient temperature
10: 1) dimethyldioxirane, 2) 40percent HF / 1) acetone, CH2Cl2, -45 deg C -> -25 deg C, 1 h; -25 deg C -> 0 deg C, 1 h, 2) MeCN, 6 h
View Scheme
Multi-step reaction with 8 steps
1: 1) TESOTf, 2,6-lutidine, 2) TBAF, AcOH / 1) CH2Cl2, 0 deg C, 1 h, 2) THF, 0 deg C, 1 h
2: 1) 2-chloro-1-methylpyridinium iodide, NEt3, 2) NEt3 / 1) CH2Cl2, reflux, 17 h, 2) EtOH, 5 h
3: 81 percent / Dess-Martin periodinane / CH2Cl2 / 3 h / Ambient temperature
4: 84 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
5: 83 percent / I2, PPh3, imidazole / toluene / 0.5 h / 75 °C
6: 74 percent / 1) KHMDS / tetrahydrofuran; toluene / 1) -78 deg C, 30 min, 2) 30 min
7: 67 percent / graphite, potassium, ZnCl2, AgOAc / tetrahydrofuran / 1.5 h / Ambient temperature
8: 1) dimethyldioxirane, 2) 40percent HF / 1) acetone, CH2Cl2, -45 deg C -> -25 deg C, 1 h; -25 deg C -> 0 deg C, 1 h, 2) MeCN, 6 h
View Scheme

C69H105NO16Si

104987-11-3

Tacrolimus

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: LiOH*H2O / tetrahydrofuran; H2O / 5 h / Ambient temperature
2: 1) TESOTf, 2,6-lutidine, 2) TBAF, AcOH / 1) CH2Cl2, 0 deg C, 1 h, 2) THF, 0 deg C, 1 h
3: 1) 2-chloro-1-methylpyridinium iodide, NEt3, 2) NEt3 / 1) CH2Cl2, reflux, 17 h, 2) EtOH, 5 h
4: 81 percent / Dess-Martin periodinane / CH2Cl2 / 3 h / Ambient temperature
5: 84 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
6: 83 percent / I2, PPh3, imidazole / toluene / 0.5 h / 75 °C
7: 74 percent / 1) KHMDS / tetrahydrofuran; toluene / 1) -78 deg C, 30 min, 2) 30 min
8: 67 percent / graphite, potassium, ZnCl2, AgOAc / tetrahydrofuran / 1.5 h / Ambient temperature
9: 1) dimethyldioxirane, 2) 40percent HF / 1) acetone, CH2Cl2, -45 deg C -> -25 deg C, 1 h; -25 deg C -> 0 deg C, 1 h, 2) MeCN, 6 h
View Scheme
Multi-step reaction with 9 steps
1: Dess-Martin periodinane / CH2Cl2 / 1 h
2: LiOH*H2O / tetrahydrofuran / 0.5 h
3: 1) TESOTf, 2,6-lutidine, 2) TBAF, AcOH / 1) CH2Cl2, 0 deg C, 1h, 2) THF, 0 deg C, 1 h
4: 47.3 mg / 2-chloro-1-methylpyridinium iodide, NET3 / CH2Cl2 / 6 h / Heating
5: 84 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
6: 83 percent / I2, PPh3, imidazole / toluene / 0.5 h / 75 °C
7: 74 percent / 1) KHMDS / tetrahydrofuran; toluene / 1) -78 deg C, 30 min, 2) 30 min
8: 67 percent / graphite, potassium, ZnCl2, AgOAc / tetrahydrofuran / 1.5 h / Ambient temperature
9: 1) dimethyldioxirane, 2) 40percent HF / 1) acetone, CH2Cl2, -45 deg C -> -25 deg C, 1 h; -25 deg C -> 0 deg C, 1 h, 2) MeCN, 6 h
View Scheme

C69H103NO16Si

104987-11-3

Tacrolimus

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: LiOH*H2O / tetrahydrofuran / 0.5 h
2: 1) TESOTf, 2,6-lutidine, 2) TBAF, AcOH / 1) CH2Cl2, 0 deg C, 1h, 2) THF, 0 deg C, 1 h
3: 47.3 mg / 2-chloro-1-methylpyridinium iodide, NET3 / CH2Cl2 / 6 h / Heating
4: 84 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
5: 83 percent / I2, PPh3, imidazole / toluene / 0.5 h / 75 °C
6: 74 percent / 1) KHMDS / tetrahydrofuran; toluene / 1) -78 deg C, 30 min, 2) 30 min
7: 67 percent / graphite, potassium, ZnCl2, AgOAc / tetrahydrofuran / 1.5 h / Ambient temperature
8: 1) dimethyldioxirane, 2) 40percent HF / 1) acetone, CH2Cl2, -45 deg C -> -25 deg C, 1 h; -25 deg C -> 0 deg C, 1 h, 2) MeCN, 6 h
View Scheme

C80H133NO15Si3

104987-11-3

Tacrolimus

Conditions
ConditionsYield
Multi-step reaction with 13 steps
1: 71 percent / TBAF / tetrahydrofuran / 2 h
2: NaHCO3, KBr, 4-methoxy-2,2,6,6-tetramethylpiperidinyloxy free radical, NaOCl / CH2Cl2 / 1.33 h / 0 °C
3: NaH2PO4, NaClO2 / 2-methyl-propan-2-ol; H2O; various solvent(s) / 2 h
4: 495 mg / diethyl ether
5: Dess-Martin periodinane / CH2Cl2 / 1 h
6: LiOH*H2O / tetrahydrofuran / 0.5 h
7: 1) TESOTf, 2,6-lutidine, 2) TBAF, AcOH / 1) CH2Cl2, 0 deg C, 1h, 2) THF, 0 deg C, 1 h
8: 47.3 mg / 2-chloro-1-methylpyridinium iodide, NET3 / CH2Cl2 / 6 h / Heating
9: 84 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
10: 83 percent / I2, PPh3, imidazole / toluene / 0.5 h / 75 °C
11: 74 percent / 1) KHMDS / tetrahydrofuran; toluene / 1) -78 deg C, 30 min, 2) 30 min
12: 67 percent / graphite, potassium, ZnCl2, AgOAc / tetrahydrofuran / 1.5 h / Ambient temperature
13: 1) dimethyldioxirane, 2) 40percent HF / 1) acetone, CH2Cl2, -45 deg C -> -25 deg C, 1 h; -25 deg C -> 0 deg C, 1 h, 2) MeCN, 6 h
View Scheme
Multi-step reaction with 11 steps
1: 71 percent / TBAF / tetrahydrofuran / 2 h
2: NaHCO3, KBr, 4-methoxy-2,2,6,6-tetramethylpiperidinyloxy free radical, NaOCl / CH2Cl2 / 1.33 h / 0 °C
3: NaH2PO4, NaClO2 / 2-methyl-propan-2-ol; H2O; various solvent(s) / 2 h
4: 1) TESOTf, 2,6-lutidine, 2) TBAF, AcOH / 1) CH2Cl2, 0 deg C, 1 h, 2) THF, 0 deg C, 1 h
5: 1) 2-chloro-1-methylpyridinium iodide, NEt3, 2) NEt3 / 1) CH2Cl2, reflux, 17 h, 2) EtOH, 5 h
6: 81 percent / Dess-Martin periodinane / CH2Cl2 / 3 h / Ambient temperature
7: 84 percent / L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
8: 83 percent / I2, PPh3, imidazole / toluene / 0.5 h / 75 °C
9: 74 percent / 1) KHMDS / tetrahydrofuran; toluene / 1) -78 deg C, 30 min, 2) 30 min
10: 67 percent / graphite, potassium, ZnCl2, AgOAc / tetrahydrofuran / 1.5 h / Ambient temperature
11: 1) dimethyldioxirane, 2) 40percent HF / 1) acetone, CH2Cl2, -45 deg C -> -25 deg C, 1 h; -25 deg C -> 0 deg C, 1 h, 2) MeCN, 6 h
View Scheme
128685-16-5, 128777-66-2

(9RS,22S)-14-<(tert-butyldimethylsilyl)oxy>-9,22-tetrahydro-24,32-bis<(triisopropylsilyl)oxy>-FK506

104987-11-3

Tacrolimus

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 82 percent / Dess-Martin periodinane / CH2Cl2 / 15 h / Ambient temperature
2: 73 percent / aq. HF / acetonitrile / 18 h / Ambient temperature
View Scheme
tacrolimus

tacrolimus

104987-11-3

Tacrolimus

Conditions
ConditionsYield
With polymer resin accoring to the invention In methanol; acetone`; water Purification / work up;
80522-42-5

triisopropylsilyl trifluoromethanesulfonate

104987-11-3

Tacrolimus

123747-39-7

C62H109NO12Si2

Conditions
ConditionsYield
With 2,6-dimethylpyridine In dichloromethane 1) 0 deg C, 1,5 h, 2) 25 deg C, 16 h;99%
104987-11-3

Tacrolimus

79-06-1

2-propenamide

1190108-68-9

C45H70N2O13

Conditions
ConditionsYield
With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In 1,2-dichloro-benzene at 150℃; for 0.0833333h; olefin cross-metathesis reaction; Microwave irradiation; Inert atmosphere;99%
104987-11-3

Tacrolimus

79-10-7

acrylic acid

1190108-69-0

C45H69NO14

Conditions
ConditionsYield
With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In 1,2-dichloro-benzene at 150℃; for 0.0833333h; olefin cross-metathesis reaction; Microwave irradiation; Inert atmosphere;99%
With Hoveyda-Grubbs catalyst second generation In 1,2-dichloro-ethane at 85℃; for 1h; Inert atmosphere; Sealed tube; Microwave irradiation;96%
With Hoveyda-Grubbs catalyst second generation In 1,2-dichloro-ethane at 85℃; for 1h; Inert atmosphere; Sealed tube;96%
Conditions
ConditionsYield
With 2,2-dimethoxy-2-phenylacetophenone In dichloromethane for 0.25h; UV-irradiation;99%
67385-09-5

2-[(tert-butoxycarbonyl)amino]-1-ethanethiol

104987-11-3

Tacrolimus

C51H84N2O14S

Conditions
ConditionsYield
With 2,2-dimethoxy-2-phenylacetophenone In dichloromethane at 20℃; for 0.25h; Solvent; Reagent/catalyst; UV-irradiation;98%
With 2,2-dimethoxy-2-phenylacetophenone In dichloromethane at 23℃; for 0.25h; Inert atmosphere; Irradiation;96%
With 2,2-dimethoxy-2-phenylacetophenone In dichloromethane at 23℃; for 0.25h; UV-irradiation; Inert atmosphere;96%
104987-11-3

Tacrolimus

107-96-0

3-mercaptopropionic acid

C47H75NO14S

Conditions
ConditionsYield
With 2,2-dimethoxy-2-phenylacetophenone In dichloromethane for 0.25h; Reagent/catalyst; UV-irradiation;98%
67-56-1

methanol

104987-11-3

Tacrolimus

133523-40-7

C45H73NO13

Conditions
ConditionsYield
With zinc(II) chloride for 3h; Ambient temperature;97%
for 3h; Heating;82%
104987-11-3

Tacrolimus

292638-85-8

acrylic acid methyl ester

C46H71NO14

Conditions
ConditionsYield
With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In 1,2-dichloro-benzene at 150℃; for 0.0833333h; olefin cross-metathesis reaction; Microwave irradiation; Inert atmosphere;97%
104987-11-3

Tacrolimus

18162-48-6

tert-butyldimethylsilyl chloride

133941-75-0

24,33-Bis-(t.butyl-dimethylsilyl)-FK 506

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide96.7%
With 1H-imidazole In N,N-dimethyl-formamide Ambient temperature;
104987-11-3

Tacrolimus

60-23-1

Cysteamine

C46H76N2O12S

Conditions
ConditionsYield
With 2,2-dimethoxy-2-phenylacetophenone In methanol for 0.25h; UV-irradiation;96%
104987-11-3

Tacrolimus

79-10-7

acrylic acid

C45H69NO14

Conditions
ConditionsYield
With Hoveyda-Grubbs catalyst second generation In 1,2-dichloro-ethane at 85℃; for 1h; Inert atmosphere; Microwave irradiation;96%
69739-34-0

t-butyldimethylsiyl triflate

104987-11-3

Tacrolimus

133941-75-0

24,33-Bis-(t.butyl-dimethylsilyl)-FK 506

Conditions
ConditionsYield
With 2,6-dimethylpyridine In dichloromethane at 0℃; for 1h; Inert atmosphere;95%
1277177-82-8

C6H12N4OS

104987-11-3

Tacrolimus

C50H81N5O13S

Conditions
ConditionsYield
With 2,2-dimethoxy-2-phenylacetophenone In dichloromethane for 0.25h; UV-irradiation;95%
52-90-4

L-Cysteine

104987-11-3

Tacrolimus

C47H76N2O14S

Conditions
ConditionsYield
With 2,2-dimethoxy-2-phenylacetophenone In methanol; water for 0.25h; UV-irradiation;95%
With 2,2-dimethoxy-2-phenylacetophenone In methanol; water at 23℃; for 0.25h; Inert atmosphere; UV-irradiation;92%
108-30-5

succinic acid anhydride

104987-11-3

Tacrolimus

C48H73NO15

Conditions
ConditionsYield
With Novozym SP435 In toluene at 45℃; for 80h; Inert atmosphere; Schlenk technique;95%
Conditions
ConditionsYield
With L-Selectride In tetrahydrofuran at -78℃; for 1.5h;90%
With tetramethylammonium triacetoxyborohydride In acetic acid; acetonitrile at -5 - 0℃; for 5h;25%
Multi-step reaction with 3 steps
1: imidazole / dimethylformamide
2: 66 percent / tetramethylammonium triacetoxyborohydride / acetonitrile; acetic acid / 5 h / -5 - 0 °C
3: 87 percent / 40percent aq. HF / acetonitrile / 2 h / 10 °C
View Scheme
104987-11-3

Tacrolimus

814-68-6

acryloyl chloride

1190108-71-4

C45H68ClNO13

Conditions
ConditionsYield
With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In isopropyl alcohol at 150℃; for 0.0833333h; olefin cross-metathesis reaction; Microwave irradiation; Inert atmosphere;88%
104987-11-3

Tacrolimus

133941-69-2

C45H71NO12

Conditions
ConditionsYield
palladium diacetate In dichloromethane Ambient temperature;87%
6911-87-1

4-bromo-N-methylaniline

104987-11-3

Tacrolimus

C51H76N2O12

Conditions
ConditionsYield
With palladium diacetate; potassium carbonate; triethylamine; tris-(o-tolyl)phosphine In N,N-dimethyl-formamide at 100℃; for 20h; Inert atmosphere; Schlenk technique;82%
With palladium diacetate; triethylamine; tris-(o-tolyl)phosphine In N,N-dimethyl-formamide at 100℃; for 20h; Heck Reaction; Inert atmosphere; Schlenk technique;62%
67-56-1

methanol

104987-11-3

Tacrolimus

124125-40-2

C45H71NO13

Conditions
ConditionsYield
With lead(IV) acetate81%
104987-11-3

Tacrolimus

124554-15-0

(E)-(1R,9S,12S,13R,14S,17R,21S,23S,24R,25S,27R)-17-Allyl-12-[(E)-2-((1R,3R,4R)-3,4-dimethoxy-cyclohexyl)-1-methyl-vinyl]-1-hydroxy-14,23,25-trimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-aza-tricyclo[22.3.1.04,9]octacos-18-ene-2,3,10,16-tetraone

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In dichloromethane at 0 - 5℃;80%
104987-11-3

Tacrolimus

(E)-(8S,11S,12R,13S,16R,20S,22S,23R,24S,26R)-16-Allyl-1,13-dihydroxy-11-[(E)-2-((1R,3R,4R)-4-hydroxy-3-methoxy-cyclohexyl)-1-methyl-vinyl]-22,24-dimethoxy-12,18,20,26-tetramethyl-10,28-dioxa-3-aza-tricyclo[21.4.1.03,8]octacos-17-ene-2,9,15,27-tetraone

Conditions
ConditionsYield
With zinc(II) chloride In dichloromethane for 15h; Ambient temperature;80%
1075-49-6

4-ethenylbenzoic acid

104987-11-3

Tacrolimus

1190108-85-0

C51H73NO14

Conditions
ConditionsYield
With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In 1,2-dichloro-benzene at 150℃; for 0.0833333h; olefin cross-metathesis reaction; Microwave irradiation; Inert atmosphere;79%
1520-21-4

4-vinyl benzylamine

104987-11-3

Tacrolimus

1190108-83-8

C50H74N2O12

Conditions
ConditionsYield
With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In 1,2-dichloro-benzene at 150℃; for 0.0833333h; olefin cross-metathesis reaction; Microwave irradiation; Inert atmosphere;79%
104987-11-3

Tacrolimus

22282-75-3

3-fluoro-4-iodopyridine

C49H71FN2O12

Conditions
ConditionsYield
With palladium diacetate; triethylamine; tris-(o-tolyl)phosphine In N,N-dimethyl-formamide at 100℃; for 24h; Heck Reaction; Inert atmosphere; Schlenk technique;78%
7677-24-9

trimethylsilyl cyanide

104987-11-3

Tacrolimus

133523-41-8

C45H70N2O12

Conditions
ConditionsYield
With potassium cyanide; 18-crown-6 ether In benzene at 23℃; for 20h;76%
104987-11-3

Tacrolimus

(3R,5S,6R)-6-[(5E,13E)-(1S,3S,7R,10S,11R,12S)-7-Allyl-10,12-dihydroxy-14-((1R,3R,4R)-4-hydroxy-3-methoxy-cyclohexyl)-1-methoxy-3,5,11,13-tetramethyl-8-oxo-tetradeca-5,13-dienyl]-5-methoxy-3-methyl-tetrahydro-pyran-2-one

Conditions
ConditionsYield
With tetra-n-butylammonium cyanide In tetrahydrofuran; water at 5℃; for 2h;76%
Downstream Products
3105-95-1
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  • Tacrolimus  FK-506  99% manufacturer in China

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    TIANFU-CHEM CAS:104987-11-3 Tacrolimus

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    Tacrolimus

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    Tacrolimus

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    Tacrolimus

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    Assay:98%-102% Appearance:White or almost white crystalline powder Storage:2-8℃ Package:in bags or customer requirements Application:Immunological suppression pharmaceutical raw material Molecular Formula C44H69NO12 Molecular Weight 804.0182

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    Tacrolimus

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    High purity Various Specifications Tacrolimus CAS:104987-11-3

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    Items Standard Result Assay 98%min ----------------------------------------------------------------------------------------------

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    104987-11-3

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  • High quality Tacrolimus Cas 104987-11-3 with favorable price

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    High quality Tacrolimus Cas 104987-11-3 with favorable price

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    104987-11-3

    Tacrolimus

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  • High Quality CAS 104987-11-3 Tacrolimus Powder

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    104987-11-3

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History

 Tacrolimus (CAS NO.104987-11-3) was among the first macrolide immunosuppressants discovered, which was discovered in 1984 by a Japanese team headed by T. Goto, T. Kino and H. Hatanaka. The name tacrolimus is derived from 'Tsukuba macrolide immunosuppressant'. Tacrolimus is owned by Astellas Pharma Inc., and is sold under the tradenames Prograf, Advagraf, and Protopic. It was first approved by the Food and Drug Administration (FDA) in 1994 use in liver transplantation, trachea, skin, cornea, and limb transplants.

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal > 200mg/kg (200mg/kg)   Journal of Antibiotics. Vol. 40, Pg. 1249, 1987.

Specification

The Tacrolimus, with the CAS registry number 104987-11-3,is also known as Tsukubaenolide. It belongs to the product categories of Pharmaceuticals; API;Chiral Reagents.Its EINECS number is 242-042-4. This chemical's molecular formula is C44H69NO12 and molecular weight is 804.02. What's more,Its systematic name is 15,19-Epoxy-3H-pyrido(2,1-c)(1,4)oxaazacyclotricosine-1,7,20,21(4H,23H)-tetrone.It is a White Crystalline Solid which is used after allogeneic organ transplant to reduce the activity of the patient's immune system and so lower the risk of organ rejection. In recent years, it has been used to suppress the inflammation associated with ulcerative colitis. It is a recent addition in the treatment of eczema, particularly atopic dermatitis, and suppresses inflammation in a similar way to steroids.

Physical properties about Tacrolimus are:
(1)ACD/LogP:  3.96; (2)# of Rule of 5 Violations:  2; (3)ACD/LogD (pH 5.5):  3.96; (4)ACD/LogD (pH 7.4):  3.96; (5)ACD/BCF (pH 5.5):  602.10; (6)ACD/BCF (pH 7.4):  600.47; (7)ACD/KOC (pH 5.5):  3398.48; (8)ACD/KOC (pH 7.4):  3389.29; (9)#H bond acceptors:  13; (10)#H bond donors:  3; (11)#Freely Rotating Bonds:  10; (12)Index of Refraction:  1.549; (13)Molar Refractivity:  214.131 cm3; (14)Molar Volume:  673.124 cm3; (15)Surface Tension:  51.2929992675781 dyne/cm; (16)Density:  1.194 g/cm3; (17)Flash Point:  481 °C; (18)Enthalpy of Vaporization:  143.946 kJ/mol; (19)Boiling Point:  871.721 °C at 760 mmHg; (20)Vapour Pressure:  0 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES:O=C3C(=O)N1CCCC[C@H]1C(=O)O[C@H](C(=C/[C@@H]2CC[C@@H](O)[C@H](OC)C2)/C)[C@H](C)[C@@H](O)CC(=O)[C@@H](/C=C(\C[C@@H](C[C@H](OC)[C@H]4O[C@]3(O)[C@H](C)C[C@@H]4OC)C)C)C\C=C;
(2)Std. InChI:InChI=1S/C44H69NO12/c1-10-13-31-19-25(2)18-26(3)20-37(54-8)40-38(55-9)22-28(5)44(52,57-40)41(49)42(50)45-17-12-11-14-32(45)43(51)56-39(29(6)34(47)24-35(31)48)27(4)21-30-15-16-33(46)36(23-30)53-7/h10,19,21,26,28-34,36-40,46-47,52H,1,11-18,20,22-24H2,2-9H3/b25-19+,27-21+/t26-,28+,29+,30-,31+,32-,33+,34-,36+,37-,38-,39+,40+,44+/m0/s1;
(3)Std. InChIKey:QJJXYPPXXYFBGM-LFZNUXCKSA-N.

The toxicity data of Tacrolimus are as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal > 200mg/kg (200mg/kg)   Journal of Antibiotics. Vol. 40, Pg. 1249, 1987.