Product Name

  • Name

    ANISOMYCIN

  • EINECS 245-269-7
  • CAS No. 22862-76-6
  • Article Data8
  • CAS DataBase
  • Density 1.21 g/cm3
  • Solubility Soluble in water at 2 mg/ml, in DMSO at 20mg/ml, and in methanol at 20mg/ml
  • Melting Point 140-141 °C
  • Formula C14H19NO4
  • Boiling Point 398.7 °C at 760 mmHg
  • Molecular Weight 265.309
  • Flash Point 194.9 °C
  • Transport Information UN 3462 6.1/PG 3
  • Appearance White crystalline solid
  • Safety 45-36-26
  • Risk Codes 25-36/37/38-20/21/22
  • Molecular Structure Molecular Structure of 22862-76-6 (ANISOMYCIN)
  • Hazard Symbols ToxicT, HarmfulXn
  • Synonyms 3,4-Pyrrolidinediol,2-(p-methoxybenzyl)-, 3-acetate, (2R,3S,4S)- (8CI);3,4-Pyrrolidinediol,2-[(4-methoxyphenyl)methyl]-, 3-acetate, [2R-(2a,3a,4b)]-;Anisomycin (6CI,7CI);(-)-Anisomycin;(2R,3S,4S)-2-(p-Methoxybenzyl)-3,4-pyrrolidinediol 3-acetate;(2R,3S,4S)-2-(p-Methoxyphenylmethyl)-3-acetoxy-4-hydroxypyrrolidine;Anisomycin, (-)-;Flagecidin;NSC 76712;
  • PSA 67.79000
  • LogP 0.83090

Synthetic route

(2R,3S,4S)-3-acetoxy-N-(benzyloxycarbonyl)-4-hydroxy-2-(4-methoxybenzyl)pyrrolidine
27958-08-3

(2R,3S,4S)-3-acetoxy-N-(benzyloxycarbonyl)-4-hydroxy-2-(4-methoxybenzyl)pyrrolidine

(-)-anisomycin
22862-76-6

(-)-anisomycin

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In ethanol under 760 Torr; for 0.25h;95%
(2R,3S,4S)-3-Acetoxy-1-(tert-butoxycarbonyl)-4-(tert-butyldimethylsilyloxy)-2-(4-methoxybenzyl)pyrrolidine
180081-83-8

(2R,3S,4S)-3-Acetoxy-1-(tert-butoxycarbonyl)-4-(tert-butyldimethylsilyloxy)-2-(4-methoxybenzyl)pyrrolidine

(-)-anisomycin
22862-76-6

(-)-anisomycin

Conditions
ConditionsYield
With hydrogenchloride In methanol at 20℃;88%
C19H27NO6
1262850-97-4

C19H27NO6

(-)-anisomycin
22862-76-6

(-)-anisomycin

Conditions
ConditionsYield
With hydrogenchloride In methanol78%
(2R,3S,4S)-3-acetoxy-1-benzyl-4-hydroxy-2-(4-methoxybenzyl)-pyrrolidine
933992-79-1

(2R,3S,4S)-3-acetoxy-1-benzyl-4-hydroxy-2-(4-methoxybenzyl)-pyrrolidine

(-)-anisomycin
22862-76-6

(-)-anisomycin

Conditions
ConditionsYield
With hydrogenchloride; hydrogen; palladium on activated charcoal In methanol; water for 3h; Yield given;
(2R,3S,4S)-3-acetoxy-4-allyloxy-1-benzyl-2-(p-methoxybenzyl)pyrrolidine
87796-48-3

(2R,3S,4S)-3-acetoxy-4-allyloxy-1-benzyl-2-(p-methoxybenzyl)pyrrolidine

(-)-anisomycin
22862-76-6

(-)-anisomycin

Conditions
ConditionsYield
With hydrogenchloride; hydrogen; palladium on activated charcoal 1.) MeOH, reflux, 2.) MeOH; Yield given. Multistep reaction;
Multi-step reaction with 2 steps
1: HCl, water / palladium-charcoal 10percent / methanol / 48 h / Heating
2: HCl, H2 / palladium-charcoal 10percent / methanol; H2O / 3 h
View Scheme
Acetic acid (1S,2R)-2-azido-1-((R)-2-bromo-1-hydroxy-ethyl)-3-(4-methoxy-phenyl)-propyl ester
173266-54-1

Acetic acid (1S,2R)-2-azido-1-((R)-2-bromo-1-hydroxy-ethyl)-3-(4-methoxy-phenyl)-propyl ester

(-)-anisomycin
22862-76-6

(-)-anisomycin

Conditions
ConditionsYield
With sodium acetate In methanol for 10h; Heating; Yield given;
C21H21NO5

C21H21NO5

(-)-anisomycin
22862-76-6

(-)-anisomycin

Conditions
ConditionsYield
With hydrogen; palladium dihydroxide In methanol; acetic acid at 20℃; under 3878.71 Torr; for 24h;76 mg
(4R,5S,6S)-5-(tert-butyldimethylsilyloxy)-4-(4-methoxybenzyl)-2-phenyl-6-vinyl-5,6-dihydro-4H-1,3-oxazine
951385-80-1

(4R,5S,6S)-5-(tert-butyldimethylsilyloxy)-4-(4-methoxybenzyl)-2-phenyl-6-vinyl-5,6-dihydro-4H-1,3-oxazine

(-)-anisomycin
22862-76-6

(-)-anisomycin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 89 percent / Bu4NF / tetrahydrofuran / 1 h / 20 °C
2: 98 percent / pyridine / CH2Cl2
3: O3; O2 / methanol / -78 °C
4: 76 mg / H2 / Pd(OH)2 / methanol; acetic acid / 24 h / 20 °C / 3878.71 Torr
View Scheme
C20H21NO3
951385-97-0

C20H21NO3

(-)-anisomycin
22862-76-6

(-)-anisomycin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 98 percent / pyridine / CH2Cl2
2: O3; O2 / methanol / -78 °C
3: 76 mg / H2 / Pd(OH)2 / methanol; acetic acid / 24 h / 20 °C / 3878.71 Torr
View Scheme
(4R,5S,6S)-4-(4-methoxybenzyl)-2-phenyl-6-vinyl-5,6-dihydro-4H-1,3-oxazin-5-yl acetate
951385-93-6

(4R,5S,6S)-4-(4-methoxybenzyl)-2-phenyl-6-vinyl-5,6-dihydro-4H-1,3-oxazin-5-yl acetate

(-)-anisomycin
22862-76-6

(-)-anisomycin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: O3; O2 / methanol / -78 °C
2: 76 mg / H2 / Pd(OH)2 / methanol; acetic acid / 24 h / 20 °C / 3878.71 Torr
View Scheme
(2S,3S)-pentene-1,2,3-triol
114489-31-5

(2S,3S)-pentene-1,2,3-triol

(-)-anisomycin
22862-76-6

(-)-anisomycin

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: DBU / acetonitrile / -30 °C
2: 1.) I2, NaHCO3, 2.) aq. HCl / 1.) MeCN, 0 deg C, 2.) MeOH, 20 deg C
3: NaHCO3 / methanol / 0 °C
5: NaHCO3 / methanol / 0 °C
6: DEAD, Ph3P, PPTS / tetrahydrofuran / 0 °C
7: imidazole / dimethylformamide / 20 °C
8: DMAP, Et3N / CH2Cl2 / 20 °C
9: 88 percent / aq. HCl / methanol / 20 °C
View Scheme
(2S,3S)-4-Amino-5-iodo-pentane-1,2,3-triol

(2S,3S)-4-Amino-5-iodo-pentane-1,2,3-triol

(-)-anisomycin
22862-76-6

(-)-anisomycin

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: NaHCO3 / methanol / 0 °C
3: NaHCO3 / methanol / 0 °C
4: DEAD, Ph3P, PPTS / tetrahydrofuran / 0 °C
5: imidazole / dimethylformamide / 20 °C
6: DMAP, Et3N / CH2Cl2 / 20 °C
7: 88 percent / aq. HCl / methanol / 20 °C
View Scheme
(S,S)-2,2-dimethyl-4-(tert-butyldimethylsilyloxy)methyl-5-hydroxymethyl-1,3-dioxolane
207123-20-4

(S,S)-2,2-dimethyl-4-(tert-butyldimethylsilyloxy)methyl-5-hydroxymethyl-1,3-dioxolane

(-)-anisomycin
22862-76-6

(-)-anisomycin

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: aq. HCl / tetrahydrofuran / 20 °C
2: DBU / acetonitrile / -30 °C
3: 1.) I2, NaHCO3, 2.) aq. HCl / 1.) MeCN, 0 deg C, 2.) MeOH, 20 deg C
4: NaHCO3 / methanol / 0 °C
6: NaHCO3 / methanol / 0 °C
7: DEAD, Ph3P, PPTS / tetrahydrofuran / 0 °C
8: imidazole / dimethylformamide / 20 °C
9: DMAP, Et3N / CH2Cl2 / 20 °C
10: 88 percent / aq. HCl / methanol / 20 °C
View Scheme
(2S,3S,4R)-4-Amino-5-(4-methoxy-phenyl)-pentane-1,2,3-triol
1053733-83-7

(2S,3S,4R)-4-Amino-5-(4-methoxy-phenyl)-pentane-1,2,3-triol

(-)-anisomycin
22862-76-6

(-)-anisomycin

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: NaHCO3 / methanol / 0 °C
2: DEAD, Ph3P, PPTS / tetrahydrofuran / 0 °C
3: imidazole / dimethylformamide / 20 °C
4: DMAP, Et3N / CH2Cl2 / 20 °C
5: 88 percent / aq. HCl / methanol / 20 °C
View Scheme
(2R,3S,4S)-1-(tert-Butoxycarbonyl)-3,4-dihydroxy-2-(4-methoxybenzyl)pyrrolidine
180081-82-7

(2R,3S,4S)-1-(tert-Butoxycarbonyl)-3,4-dihydroxy-2-(4-methoxybenzyl)pyrrolidine

(-)-anisomycin
22862-76-6

(-)-anisomycin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: imidazole / dimethylformamide / 20 °C
2: DMAP, Et3N / CH2Cl2 / 20 °C
3: 88 percent / aq. HCl / methanol / 20 °C
View Scheme
[(1R,2S,3S)-2,3,4-Trihydroxy-1-(4-methoxy-benzyl)-butyl]-carbamic acid tert-butyl ester
180081-81-6

[(1R,2S,3S)-2,3,4-Trihydroxy-1-(4-methoxy-benzyl)-butyl]-carbamic acid tert-butyl ester

(-)-anisomycin
22862-76-6

(-)-anisomycin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: DEAD, Ph3P, PPTS / tetrahydrofuran / 0 °C
2: imidazole / dimethylformamide / 20 °C
3: DMAP, Et3N / CH2Cl2 / 20 °C
4: 88 percent / aq. HCl / methanol / 20 °C
View Scheme
(2R,3S,4S)-1-(tert-Butoxycarbonyl)-4-(tert-butyldimethylsilyloxy)-3-hydroxy-2-(4-methoxybenzyl)pyrrolidine
249617-08-1

(2R,3S,4S)-1-(tert-Butoxycarbonyl)-4-(tert-butyldimethylsilyloxy)-3-hydroxy-2-(4-methoxybenzyl)pyrrolidine

(-)-anisomycin
22862-76-6

(-)-anisomycin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: DMAP, Et3N / CH2Cl2 / 20 °C
2: 88 percent / aq. HCl / methanol / 20 °C
View Scheme
2,2,2-Trichloro-acetimidic acid (1S,2S)-2-(2,2,2-trichloro-acetimidoyloxy)-1-(2,2,2-trichloro-acetimidoyloxymethyl)-but-3-enyl ester
180081-74-7

2,2,2-Trichloro-acetimidic acid (1S,2S)-2-(2,2,2-trichloro-acetimidoyloxy)-1-(2,2,2-trichloro-acetimidoyloxymethyl)-but-3-enyl ester

(-)-anisomycin
22862-76-6

(-)-anisomycin

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 1.) I2, NaHCO3, 2.) aq. HCl / 1.) MeCN, 0 deg C, 2.) MeOH, 20 deg C
2: NaHCO3 / methanol / 0 °C
4: NaHCO3 / methanol / 0 °C
5: DEAD, Ph3P, PPTS / tetrahydrofuran / 0 °C
6: imidazole / dimethylformamide / 20 °C
7: DMAP, Et3N / CH2Cl2 / 20 °C
8: 88 percent / aq. HCl / methanol / 20 °C
View Scheme
((1S,2S,3S)-2,3,4-Trihydroxy-1-iodomethyl-butyl)-carbamic acid tert-butyl ester
180081-77-0

((1S,2S,3S)-2,3,4-Trihydroxy-1-iodomethyl-butyl)-carbamic acid tert-butyl ester

(-)-anisomycin
22862-76-6

(-)-anisomycin

Conditions
ConditionsYield
Multi-step reaction with 6 steps
2: NaHCO3 / methanol / 0 °C
3: DEAD, Ph3P, PPTS / tetrahydrofuran / 0 °C
4: imidazole / dimethylformamide / 20 °C
5: DMAP, Et3N / CH2Cl2 / 20 °C
6: 88 percent / aq. HCl / methanol / 20 °C
View Scheme
divinylcarbinol
922-65-6

divinylcarbinol

(-)-anisomycin
22862-76-6

(-)-anisomycin

Conditions
ConditionsYield
Multi-step reaction with 13 steps
1: D-(-)-DIPT, TBHP, Ti(O-i-Pr)4 / CH2Cl2 / -20 °C
2: Et3N, DMAP / CH2Cl2
3: 85 percent / copper(I) iodide / tetrahydrofuran / -10 °C
4: 94 percent / pyridine / CH2Cl2 / Ambient temperature
5: NaN3 / dimethylformamide / 7 h / 80 °C
6: 2N aq. HCl / 0.5 h
7: 95 percent / OsO4, K3Fe(CN)6, K2CO3, DHQ-CLB, water / 2-methyl-propan-2-ol
8: 89 percent / imidazole / dimethylformamide / 0 °C
9: pyridine / CH2Cl2 / 2 h / Ambient temperature
10: pyridine / 4 h / Ambient temperature
11: 91 percent / n-Bu4NF / tetrahydrofuran / 1 h / 0 °C
12: 90 percent / lithium bromide / acetic acid; tetrahydrofuran / 24 h / Ambient temperature
13: NaOAc / methanol / 10 h / Heating
View Scheme
(2S,3R)-1,2-epoxy-4-penten-3-ol
102490-00-6

(2S,3R)-1,2-epoxy-4-penten-3-ol

(-)-anisomycin
22862-76-6

(-)-anisomycin

Conditions
ConditionsYield
Multi-step reaction with 12 steps
1: Et3N, DMAP / CH2Cl2
2: 85 percent / copper(I) iodide / tetrahydrofuran / -10 °C
3: 94 percent / pyridine / CH2Cl2 / Ambient temperature
4: NaN3 / dimethylformamide / 7 h / 80 °C
5: 2N aq. HCl / 0.5 h
6: 95 percent / OsO4, K3Fe(CN)6, K2CO3, DHQ-CLB, water / 2-methyl-propan-2-ol
7: 89 percent / imidazole / dimethylformamide / 0 °C
8: pyridine / CH2Cl2 / 2 h / Ambient temperature
9: pyridine / 4 h / Ambient temperature
10: 91 percent / n-Bu4NF / tetrahydrofuran / 1 h / 0 °C
11: 90 percent / lithium bromide / acetic acid; tetrahydrofuran / 24 h / Ambient temperature
12: NaOAc / methanol / 10 h / Heating
View Scheme
(3S,4S)-trimethylsilyloxy oxirane
173328-15-9

(3S,4S)-trimethylsilyloxy oxirane

(-)-anisomycin
22862-76-6

(-)-anisomycin

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1: 85 percent / copper(I) iodide / tetrahydrofuran / -10 °C
2: 94 percent / pyridine / CH2Cl2 / Ambient temperature
3: NaN3 / dimethylformamide / 7 h / 80 °C
4: 2N aq. HCl / 0.5 h
5: 95 percent / OsO4, K3Fe(CN)6, K2CO3, DHQ-CLB, water / 2-methyl-propan-2-ol
6: 89 percent / imidazole / dimethylformamide / 0 °C
7: pyridine / CH2Cl2 / 2 h / Ambient temperature
8: pyridine / 4 h / Ambient temperature
9: 91 percent / n-Bu4NF / tetrahydrofuran / 1 h / 0 °C
10: 90 percent / lithium bromide / acetic acid; tetrahydrofuran / 24 h / Ambient temperature
11: NaOAc / methanol / 10 h / Heating
View Scheme
(2S,3R)-1-(4-Methoxy-phenyl)-3-trimethylsilanyloxy-pent-4-en-2-ol
173266-46-1

(2S,3R)-1-(4-Methoxy-phenyl)-3-trimethylsilanyloxy-pent-4-en-2-ol

(-)-anisomycin
22862-76-6

(-)-anisomycin

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: 94 percent / pyridine / CH2Cl2 / Ambient temperature
2: NaN3 / dimethylformamide / 7 h / 80 °C
3: 2N aq. HCl / 0.5 h
4: 95 percent / OsO4, K3Fe(CN)6, K2CO3, DHQ-CLB, water / 2-methyl-propan-2-ol
5: 89 percent / imidazole / dimethylformamide / 0 °C
6: pyridine / CH2Cl2 / 2 h / Ambient temperature
7: pyridine / 4 h / Ambient temperature
8: 91 percent / n-Bu4NF / tetrahydrofuran / 1 h / 0 °C
9: 90 percent / lithium bromide / acetic acid; tetrahydrofuran / 24 h / Ambient temperature
10: NaOAc / methanol / 10 h / Heating
View Scheme
(3R,4R)-4-Azido-5-(4-methoxy-phenyl)-pent-1-en-3-ol
173266-47-2

(3R,4R)-4-Azido-5-(4-methoxy-phenyl)-pent-1-en-3-ol

(-)-anisomycin
22862-76-6

(-)-anisomycin

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 95 percent / OsO4, K3Fe(CN)6, K2CO3, DHQ-CLB, water / 2-methyl-propan-2-ol
2: 89 percent / imidazole / dimethylformamide / 0 °C
3: pyridine / CH2Cl2 / 2 h / Ambient temperature
4: pyridine / 4 h / Ambient temperature
5: 91 percent / n-Bu4NF / tetrahydrofuran / 1 h / 0 °C
6: 90 percent / lithium bromide / acetic acid; tetrahydrofuran / 24 h / Ambient temperature
7: NaOAc / methanol / 10 h / Heating
View Scheme
{(R)-1-[(R)-1-Azido-2-(4-methoxy-phenyl)-ethyl]-allyloxy}-trimethyl-silane

{(R)-1-[(R)-1-Azido-2-(4-methoxy-phenyl)-ethyl]-allyloxy}-trimethyl-silane

(-)-anisomycin
22862-76-6

(-)-anisomycin

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 2N aq. HCl / 0.5 h
2: 95 percent / OsO4, K3Fe(CN)6, K2CO3, DHQ-CLB, water / 2-methyl-propan-2-ol
3: 89 percent / imidazole / dimethylformamide / 0 °C
4: pyridine / CH2Cl2 / 2 h / Ambient temperature
5: pyridine / 4 h / Ambient temperature
6: 91 percent / n-Bu4NF / tetrahydrofuran / 1 h / 0 °C
7: 90 percent / lithium bromide / acetic acid; tetrahydrofuran / 24 h / Ambient temperature
8: NaOAc / methanol / 10 h / Heating
View Scheme
(2S,3S,4R)-4-Azido-5-(4-methoxy-phenyl)-pentane-1,2,3-triol

(2S,3S,4R)-4-Azido-5-(4-methoxy-phenyl)-pentane-1,2,3-triol

(-)-anisomycin
22862-76-6

(-)-anisomycin

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 89 percent / imidazole / dimethylformamide / 0 °C
2: pyridine / CH2Cl2 / 2 h / Ambient temperature
3: pyridine / 4 h / Ambient temperature
4: 91 percent / n-Bu4NF / tetrahydrofuran / 1 h / 0 °C
5: 90 percent / lithium bromide / acetic acid; tetrahydrofuran / 24 h / Ambient temperature
6: NaOAc / methanol / 10 h / Heating
View Scheme
Acetic acid (1S,2R)-2-azido-3-(4-methoxy-phenyl)-1-(S)-oxiranyl-propyl ester
173266-52-9

Acetic acid (1S,2R)-2-azido-3-(4-methoxy-phenyl)-1-(S)-oxiranyl-propyl ester

(-)-anisomycin
22862-76-6

(-)-anisomycin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 90 percent / lithium bromide / acetic acid; tetrahydrofuran / 24 h / Ambient temperature
2: NaOAc / methanol / 10 h / Heating
View Scheme
Methanesulfonic acid (1S,2R)-1-(4-methoxy-benzyl)-2-trimethylsilanyloxy-but-3-enyl ester
173266-56-3

Methanesulfonic acid (1S,2R)-1-(4-methoxy-benzyl)-2-trimethylsilanyloxy-but-3-enyl ester

(-)-anisomycin
22862-76-6

(-)-anisomycin

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: NaN3 / dimethylformamide / 7 h / 80 °C
2: 2N aq. HCl / 0.5 h
3: 95 percent / OsO4, K3Fe(CN)6, K2CO3, DHQ-CLB, water / 2-methyl-propan-2-ol
4: 89 percent / imidazole / dimethylformamide / 0 °C
5: pyridine / CH2Cl2 / 2 h / Ambient temperature
6: pyridine / 4 h / Ambient temperature
7: 91 percent / n-Bu4NF / tetrahydrofuran / 1 h / 0 °C
8: 90 percent / lithium bromide / acetic acid; tetrahydrofuran / 24 h / Ambient temperature
9: NaOAc / methanol / 10 h / Heating
View Scheme
(2S,3S,4R)-4-Azido-1-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-phenyl)-pentane-2,3-diol

(2S,3S,4R)-4-Azido-1-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-phenyl)-pentane-2,3-diol

(-)-anisomycin
22862-76-6

(-)-anisomycin

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: pyridine / CH2Cl2 / 2 h / Ambient temperature
2: pyridine / 4 h / Ambient temperature
3: 91 percent / n-Bu4NF / tetrahydrofuran / 1 h / 0 °C
4: 90 percent / lithium bromide / acetic acid; tetrahydrofuran / 24 h / Ambient temperature
5: NaOAc / methanol / 10 h / Heating
View Scheme
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

(-)-anisomycin
22862-76-6

(-)-anisomycin

C19H27NO6
1262850-97-4

C19H27NO6

Conditions
ConditionsYield
With sodium hydrogencarbonate In tetrahydrofuran; water at 20℃; for 3h;100%
(-)-anisomycin
22862-76-6

(-)-anisomycin

propargyl bromide
106-96-7

propargyl bromide

(2R,3S,4S)-3-acetoxy-4-hydroxy-2-(4-methoxybenzyl)-1-propargylpyrrolidine

(2R,3S,4S)-3-acetoxy-4-hydroxy-2-(4-methoxybenzyl)-1-propargylpyrrolidine

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 9h;95%
(-)-anisomycin
22862-76-6

(-)-anisomycin

benzyl bromide
100-39-0

benzyl bromide

(2R,3S,4S)-3-acetoxy-1-benzyl-4-hydroxy-2-(4-methoxybenzyl)-pyrrolidine
933992-79-1

(2R,3S,4S)-3-acetoxy-1-benzyl-4-hydroxy-2-(4-methoxybenzyl)-pyrrolidine

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 4h;89%

Anisomycin Chemical Properties

Molecular Formula: C14H19NO4
Molar mass: 265.305 g/mol
EINECS: 245-269-7
Form: Solid
Color: White
Density: 1.21 g/cm3
Flash Point: 194.9 °C
Melting point: 140-141 °C
Storage temp: 2-8 °C
Appearance: Crystalline
Index of Refraction: 1.557
Boiling Point: 398.7 °C at 760 mmHg
Vapour Pressure: 4.5E-07 mmHg at 25 °C
Solubility: Methanol: 20 mg/mL, clear, colorless to faintly yellow
Stable: Stable. Incompatible with strong oxidizing agents.
Product categories of Anisomycin (CAS NO.22862-76-6): Antibiotics;Protein Kinase
Structure of Anisomycin (CAS NO.22862-76-6):
                                   

Anisomycin Uses

 Anisomycin (CAS NO.22862-76-6) has wide usage as a protein biosynthesis inhibitor. It is used as a component of Martin Lewis Agar, an in- vitro diagnostic product which is used extensively in the United States for the selective isolation of Neisseria gonorrhoeae and Neisseria meningitidis. Mawji et al. showed that anisomycin can sensitize metastatic epithelial cells to anoikis and reduce circulating tumor cell implantation in vivo by using a novel high-throughput screening assay. Anisomycin achieved this anti-metastatic activity in part by decreasing the abundance of the death receptor inhibiting protein FLIP.

Anisomycin Production

Although pyrrolidine-based structure of Anisomycin (CAS NO.22862-76-6) suggests that it is derived from proline, the results from the experiments indicated that tyrosine, glycine, methionine, and acetate are the primary precursors for the biosynthesis of anisomycin. The methord is:

Anisomycin Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LD oral > 200mg/kg (200mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING Antibiotics and Chemotherapy Vol. 5, Pg. 490, 1955.
dog LD intramuscular > 100mg/kg (100mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING Antibiotics and Chemotherapy Vol. 5, Pg. 490, 1955.
dog LD intravenous > 100mg/kg (100mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING Antibiotics and Chemotherapy Vol. 5, Pg. 490, 1955.
dog LD oral > 300mg/kg (300mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING Antibiotics and Chemotherapy Vol. 5, Pg. 490, 1955.
guinea pig LDLo oral 300mg/kg (300mg/kg)   Antibiotics and Chemotherapy Vol. 5, Pg. 490, 1955.
monkey LD intramuscular > 50mg/kg (50mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING Antibiotics and Chemotherapy Vol. 5, Pg. 490, 1955.
monkey LD oral > 300mg/kg (300mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING Antibiotics and Chemotherapy Vol. 5, Pg. 490, 1955.
monkey LDLo intravenous 200mg/kg (200mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING Antibiotics and Chemotherapy Vol. 5, Pg. 490, 1955.
mouse LD50 intraperitoneal 400mg/kg (400mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION		 Antibiotics and Chemotherapy Vol. 5, Pg. 490, 1955.
mouse LD50 intravenous 10mg/kg (10mg/kg)   "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980Vol. 5, Pg. 77, 1981.
mouse LD50 oral 148mg/kg (148mg/kg)   Antibiotics and Chemotherapy Vol. 5, Pg. 490, 1955.
mouse LD50 subcutaneous 600mg/kg (600mg/kg)   Antibiotics and Chemotherapy Vol. 5, Pg. 490, 1955.
rabbit LD oral > 200mg/kg (200mg/kg)   Antibiotics and Chemotherapy Vol. 5, Pg. 490, 1955.
rat LD50 intraperitoneal 345mg/kg (345mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION		 Antibiotics and Chemotherapy Vol. 5, Pg. 490, 1955.
rat LD50 intravenous 167mg/kg (167mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION		 Antibiotics and Chemotherapy Vol. 5, Pg. 490, 1955.
rat LD50 oral 72mg/kg (72mg/kg)   Antibiotics and Chemotherapy Vol. 5, Pg. 490, 1955.
rat LD50 subcutaneous 230mg/kg (230mg/kg)   Antibiotics and Chemotherapy Vol. 5, Pg. 490, 1955.

Anisomycin Safety Profile

Poison by ingestion, intraperitoneal, subcutaneous, and intravenous routes. When heated to decomposition it emits toxic fumes of NOx.
 

Hazard Codes: ToxicTHarmfulXn
Risk Statements: 25-36/37/38-20/21/22
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed. 
R25 :Toxic if swallowed. 
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 45-36-26
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36:Wear suitable protective clothing. 
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)

Anisomycin Specification

 Anisomycin ,its cas register number is 22862-76-6. It also can be called Flagecidin ; 4-Hydroxy-2-(4-methoxybenzyl)-3-pyrrolidinylacetat ; Acétate de 4-hydroxy-2-(4-méthoxybenzyl)-3-pyrrolidinyle and 3,4-pyrrolidinediol, 2-[(4-methoxyphenyl)methyl]-, 3-acetate . It is inactive against bacteria, and can activate stress-activated protein kinases, MAP kinase and other signal transduction pathways. Partial inhibition of DNA synthesis occurs at anisomycin concentrations that effect 95% inhibition of protein synthesis.

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