22862-76-6

Basic information

• Product Name: ANISOMYCIN
• Synonyms: (2R,3S,4S)-2-(4-METHOXYBENZYL)-3,4-PYRROLIDINEDOIL-3-ACETATE;(2R,3S,4S)-2-[(4-METHOXYPHENYL)METHYL]-3,4-PYRROLIDINEDIOL 3-ACETATE;2-(P-METHOXYBENZYL)-3,4-PYRROLIDINEDIOL-3-ACETATE;2-P-METHOXYPHENYLMETHYL-3-ACETOXY-4-HYDROXYPYRROLIDINE;1,4,5-trideoxy-1,4-imino-5-(p-methoxyphenyl)-D-xylo-pentitol 3-acetate;ANISOMYCIN FROM STREPTOMYCES GRISEOLUS;3,4-Pyrrolidinediol, 2-(4-methoxyphenyl)methyl-, 3-acetate, (2R,3S,4S)-;(2R,3S,4S)-2-(p-Methoxybenzyl)-3,4-pyrrolidinediol 3-acetate
• CAS NO: 22862-76-6
• Molecular Formula: C₁₄H₁₉NO₄
• Molecular Weight: 265.3
• EINECS: 245-269-7
• Product Categories: Antibiotics;Protein Kinase;antibiotic
• Mol File: 22862-76-6.mol
• Article Data: 7

Chemical Properties

• Melting Point: 140-141 C
• Boiling Point: 408.52°C (rough estimate)
• Flash Point: 87℃
• Appearance: white/solid
• Density: 1.1356 (rough estimate)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.5230 (estimate)
• Storage Temp.: 2-8°C
• Solubility: methanol: 20 mg/mL, clear, colorless to faintly yellow
• PKA: 7.9(at 25℃)
• Water Solubility: Soluble in water at 2 mg/ml, in DMSO at 20mg/ml, and in methanol at 20mg/ml
• Stability: Stable. Incompatible with strong oxidizing agents.
• Merck: 14,670
• BRN: 20705
• CAS DataBase Reference: ANISOMYCIN(CAS DataBase Reference)
• NIST Chemistry Reference: ANISOMYCIN(22862-76-6)
• EPA Substance Registry System: ANISOMYCIN(22862-76-6)

Safety Data

• Hazard Codes: T,Xn
• Statements: 25-36/37/38-20/21/22
• Safety Statements: 45-36-26
• RIDADR: UN 3462 6.1/PG 3
• WGK Germany: 3
• RTECS: BZ9800000
• F: 3-10
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 22862-76-6(Hazardous Substances Data)

Usage

Description

Anisomycin is a phenylmethylenepyrrolidine antibiotic that was first isolated from Streptomyces griseolus in 1954. It is known for its antiprotozoan and antifungal activities. Anisomycin functions as an inhibitor of protein synthesis by binding to the 60S ribosomal subunit. It has also been found to induce amnesia in animal models and has more recently been shown to induce apoptosis, act as a selective signaling agonist, activate mitogen-activated protein (MAP) kinases, and exhibit immunomodulatory effects on T cells. Anisomycin is characterized by its crystalline chemical properties.

Uses

Used in Pharmaceutical Applications:
Anisomycin is used as an antiparasitic agent for its antiprotozoan and antifungal activities. It acts as a protein synthesis inhibitor by blocking translation, which can be useful in treating certain parasitic infections.
Used in Cancer Research:
Anisomycin is used as an antineoplastic agent, inducing apoptosis and sensitizing cells to anoikis. It also acts as a potent activator of stress-activated protein kinases (JNK/SAPK) and p38 MAP kinase, which can be beneficial in cancer research and treatment.
Used in Signal Transduction Research:
Anisomycin is used as a potent signaling agonist to selectively elicit homologous desensitization of immediate early gene induction (c-fos, fosB, c-jun, junB, and junD). This makes it a valuable tool in studying signal transduction pathways and their role in various cellular processes.
Used in Immunological Research:
Anisomycin is used to study its immunomodulatory effects on T cells, which can provide insights into the immune system and potential applications in immunological research and therapy.

Biological Activity

Protein synthesis inhibitor (blocks translation). Potent activator of stress-activated protein kinases (JNK/SAPK) and p38 MAP kinase. Acts as a potent signaling agonist to selectively elicit homologous desensitization of immediate early gene induction (c-fos, fosB, c-jun, junB and junD).

Biochem/physiol Actions

Antibiotic isolated from Streptomyces griseolus that inhibits protein synthesis. Acts by inhibiting peptidyl transferase activity in eukaryote ribosomes. Reported to induce apoptosis in a variety of cells including promyelocytic leukemia cells, Jurkat cells, ventricular myocytes, and colon adenocarcinoma cells. Initiates intracellular signals and immediate early gene induction. Selective signaling agonist. Potent Jun-NH2 terminal kinase (JNK) agonist. Activates mitogen-activated protein (MAP) kinases (JNK/SAPK and p38/RK). Antiprotozoal agent.

References

1) Hazzalin?et al. (1998),?Anisomycin Selectively Desensitizes Signalling Components Involved in Stress Kinase Activation and fos and jun Induction; Mol. Cell. Bio.,?8?1844 2) Mawji?et al. (2007),?A Chemical Screen Identifies Anisomycin as an Anoikis Sensitizer That Functions by Decreasing FLIP Protein Synthesis; Cancer Res.,?67?8307

InChI:InChI=1/C14H19NO4/c1-9(16)19-14-12(15-8-13(14)17)7-10-3-5-11(18-2)6-4-10/h3-6,12-15,17H,7-8H2,1-2H3/p+1/t12-,13+,14+/m1/s1

Synthetic route

(2R,3S,4S)-3-acetoxy-N-(benzyloxycarbonyl)-4-hydroxy-2-(4-methoxybenzyl)pyrrolidine (27958-08-3) → (-)-anisomycin (22862-76-6)

Conditions	Yield
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) → (-)-anisomycin (22862-76-6)

Conditions	Yield
With hydrogenchloride In methanol at 20℃;	88%

C19H27NO6 (1262850-97-4) → (-)-anisomycin (22862-76-6)

Conditions	Yield
With hydrogenchloride In methanol	78%

(2R,3S,4S)-3-acetoxy-1-benzyl-4-hydroxy-2-(4-methoxybenzyl)-pyrrolidine (933992-79-1) → (-)-anisomycin (22862-76-6)

Conditions	Yield
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) → (-)-anisomycin (22862-76-6)

Conditions	Yield
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) → (-)-anisomycin (22862-76-6)

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

C21H21NO5 → (-)-anisomycin (22862-76-6)

Conditions	Yield
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) → (-)-anisomycin (22862-76-6)

Conditions	Yield
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) → (-)-anisomycin (22862-76-6)

Conditions	Yield
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) → (-)-anisomycin (22862-76-6)

Conditions	Yield
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) → (-)-anisomycin (22862-76-6)

Conditions	Yield
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 → (-)-anisomycin (22862-76-6)

Conditions	Yield
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) → (-)-anisomycin (22862-76-6)

Conditions

Yield

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) → (-)-anisomycin (22862-76-6)

Conditions	Yield
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) → (-)-anisomycin (22862-76-6)

Conditions	Yield
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) → (-)-anisomycin (22862-76-6)

Conditions	Yield
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) → (-)-anisomycin (22862-76-6)

Conditions	Yield
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) → (-)-anisomycin (22862-76-6)

Conditions	Yield
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) → (-)-anisomycin (22862-76-6)

Conditions	Yield
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) → (-)-anisomycin (22862-76-6)

Conditions

Yield

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) → (-)-anisomycin (22862-76-6)

Conditions

Yield

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) → (-)-anisomycin (22862-76-6)

Conditions

Yield

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) → (-)-anisomycin (22862-76-6)

Conditions

Yield

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) → (-)-anisomycin (22862-76-6)

Conditions

Yield

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 → (-)-anisomycin (22862-76-6)

Conditions

Yield

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 → (-)-anisomycin (22862-76-6)

Conditions	Yield
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) → (-)-anisomycin (22862-76-6)

Conditions	Yield
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) → (-)-anisomycin (22862-76-6)

Conditions

Yield

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 → (-)-anisomycin (22862-76-6)

Conditions	Yield
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) + (-)-anisomycin (22862-76-6) → C19H27NO6 (1262850-97-4)

Conditions	Yield
With sodium hydrogencarbonate In tetrahydrofuran; water at 20℃; for 3h;	100%

(-)-anisomycin (22862-76-6) + propargyl bromide (106-96-7) → (2R,3S,4S)-3-acetoxy-4-hydroxy-2-(4-methoxybenzyl)-1-propargylpyrrolidine

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 9h;	95%

(-)-anisomycin (22862-76-6) + benzyl bromide (100-39-0) → (2R,3S,4S)-3-acetoxy-1-benzyl-4-hydroxy-2-(4-methoxybenzyl)-pyrrolidine (933992-79-1)

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

Upstream product

• 17355-24-7 methyl (R)-2-acetamido-3-(4-methoxyphenyl)propanoate 
• 19764-32-0 Ac-D-Tyrosine 
• 556-02-5 tyrosine 
• 1380403-20-2 C₁₄H₁₉NO₄ 
• 1380403-17-7 C₁₄H₁₉NO₃ 
• 1380403-14-4 C₁₄H₁₇NO₃ 
• 1380403-11-1 (R)-N-(1-(4-methoxyphenyl)-3-oxopropan-2-yl)acetamide 
• 1380403-08-6 C₁₂H₁₇NO₃ 
• 1380403-25-7 C₂₀H₃₁NO₉S 
• 1380403-23-5 C₁₉H₂₉NO₇ 
• 1380403-22-4 C₁₄H₁₇NO₃ 
• 1262850-97-4 C₁₉H₂₇NO₆ 
• 824-94-2 p-methoxybenzyl chloride 
• 99394-31-7 (2R,3S,4R)-3,4-dihydroxy-2-(p-methoxybenzyl)pyrrolidine hydrochloride 

Downstream Products

• 1262850-97-4 C₁₉H₂₇NO₆ 
• 933992-79-1 (2R,3S,4S)-3-acetoxy-1-benzyl-4-hydroxy-2-(4-methoxybenzyl)-pyrrolidine 

Relevant articles and documents

Concise synthesis of (-)-anisomycin

The antibiotic (-)-anisomycin was synthesized starting from d-tyrosine using Sharpless asymmetric epoxidation as a key reaction followed by formation and hydrolysis of oxazoline set up all chiral center.

Asymmetric amidation of (2S,3S)-pent-4-ene-1,2,3-triol. Total syntheses of (-)-anisomycin and (+)-polyoxamic acid

Intramolecular iodoamidation of pentenetriol 2 provides trihydroxy carbamate 8 in 94% de and was elaborated to (-)-anisomycin 15 and (+)-polyoxamic acid 19.

Highly selective total synthesis of enantiomerically pure (-)-anisomycin

-