220736-25-4

Basic information

• Product Name: CYTOXAZONE
• Synonyms: (-)-Cytoxazone;Cytoxazone
• CAS NO: 220736-25-4
• Molecular Formula: C11H13NO4
• Molecular Weight: 223.227
• Mol File: 220736-25-4.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: CYTOXAZONE(CAS DataBase Reference)
• NIST Chemistry Reference: CYTOXAZONE(220736-25-4)
• EPA Substance Registry System: CYTOXAZONE(220736-25-4)

Safety Data

• Hazardous Substances Data: 220736-25-4(Hazardous Substances Data)

Upstream product

• 104171-26-8 (1R,2R)-1-(4-Methoxy-phenyl)-propane-1,2,3-triol 
• 1379528-94-5 (S)-N-((S)-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)(p-methoxyphenyl)methyl)-2-methyl propane-2-sulfinamide 
• 1379528-98-9 (2S,3S)-3-amino-3-(4-methoxyphenyl)propane-1,2-diol hydrochloride 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 237736-16-2 (4R,5R)-5-(tert-butyldiphenylsilyloxymethyl)-4-(4-methoxyphenyl)oxazolidin-2-one 
• 701975-97-5 [(4R,5R)-4-(4-methoxyphenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl (1S,4R)-4,7,7-trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylate 
• 929517-37-3 (E)-(R)-N-(4-methoxybenzylidene)-1-(4-methoxyphenyl)ethanamine 
• 929517-32-8 (3S,4R)-3-hydroxy-4-(4-methoxyphenyl)-1-[(R)-1-(4-methoxyphenyl)ethyl]azetidin-2-one 
• 929517-33-9 methyl (2S,3R)-2-hydroxy-3-(4-methoxyphenyl)-3-[((R)-1-(4-methoxyphenyl)ethyl)amino]propionate 
• 929517-34-0 methyl (2S,3R)-3-((tert-butoxycarbonyl)amino)-2-hydroxy-3-(4-methoxyphenyl)propanoate 
• 929517-39-5 (1R,2R)-1-((tert-butoxycarbonyl)amino)-3-methoxy-1-(4-methoxyphenyl)-3-oxopropan-2-yl 4-nitrobenzoate 
• 929517-35-1 (2R,3R)-methyl 3-[N-(tert-butoxycarbonyl)amino]-2-hydroxy-3-(p-methoxyphenyl)propanoate 
• 865565-43-1 (1R,2S)-1,2-dimethoxy-1-(p-methoxyphenyl)but-3-ene 
• 865565-65-7 (2R,3R)-2-methoxy-3-(methoxycarbonylamino)-3-(p-methoxyphenyl)propan-1-ol 

Downstream Products

• 1613057-73-0 ((4R,5R)-3-(3-fluoro-4-morpholinophenyl)-4-(4-methoxyphenyl)-2-oxooxazolidin-5-yl)methyl benzoate 
• 1613057-72-9 3-(((4R,5R)-3-(3-fluoro-4-morpholinophenyl)-4-(4-methoxyphenyl)-2-oxooxazolidin-5-yl)methoxy)-3-oxopropyl acrylate 
• 1613057-71-8 (4R,5R)-3-(3-fluoro-4-morpholinophenyl)-5-(hydroxymethyl)-4-(4-methoxyphenyl)oxazolidin-2-one 
• 254761-52-9 (4R,5R)-5-(((tert-butyldimethylsilyl)oxy)methyl)-4-(4-methoxyphenyl)oxazolidin-2-one 

Relevant articles and documents

Short-step and scalable synthesis of (±)-cytoxazone

A five-step and scalable synthesis of racemic cytoxazone, a novel cytokine modulator, was accomplished in a total yield of 51% from p-methoxycinnamyl alcohol without any protective groups. The keystep was the new one-pot azidohydroxylation procedure by th

DDQ mediated stereoselective intermolecular benzylic C[sbnd]N bond formation: Synthesis of (?)-cytoxazone, (?)-4-epi-cytoxazone and their analogues and immunological evaluation of their cytokine modulating activity

A short and efficient strategy for the synthesis of (?)-cytoxazone, (?)-4-epi-cyoxazone and their analogues by using DDQ mediated diastereoselective intermolecular benzylic amination has been described. Immunological evaluation of their cytokine modulating activity revealed that the change of hydroxy methyl to methyl group increased the cellular immunity in in-vitro cultures. Changes in the stereochemistry of oxazolidine haven't influenced the biological activity.

Chemoenzymatic synthesis of all four cytoxazone stereoisomers

Racemic cytoxazone (±-5) was synthesized starting from easily available glycidic ester (±)-1 by nucleophilic epoxide ring opening, followed by 2-oxazolidinone ring construction and calcium chloride/sodium borohydride reduction of the intermediary ester (±

Short synthesis of epi-cytoxazone via oxazoline formation through intramolecular benzylic substitution of a bis-trichloroacetimidate

A short and efficient method for synthesizing epi-cytoxazone via the corresponding oxazoline intermediate was developed. The formation of the oxazoline ring, which proceeds through an SN1 mechanism to ensure that the trans-oxazoline stereochemistry is retained, was induced by intramolecular benzylic substitution of a 1,2-bis-trichloroacetimidate, starting from the known enantiomerically pure diol.

Preparation method of (-) - Cytoxazone and (+) -4 - epi-Cytoxazone

The preparation method of (-) - Cytoxazone and (+) -4 - epi-Cytoxazone takes D - p-hydroxyphenylglycine as a raw material, the intermediate 2 is obtained through methyl esterification reaction under catalysis of thionyl chloride, and then the amino is protected with Boc anhydride to obtain the intermediate 3. The compound 4 is obtained by using potassium carbonate as a base and reacting with methyl iodide under reflux conditions. The methyl ester was reduced with sodium borohydride/lithium chloride to give the primary alcohol compound 5. An intermediate IBX is then obtained with 6 primary alcohol, then reacted with acetone cyanohydrin SN2 to give intermediate 7, and the intermediate 8 is obtained by reacting with the methanol solution of hydrogen chloride to obtain two five-membered ring compound compounds 9 and 10, respectively, with sodium borohydride to obtain (-) - Cytoxazone and its isomers (+) -4 - epi-Cytoxtoxtoxtoxol, respectively.

Stereoselective synthesis of (?)-cytoxazone and its unnatural congener (+)-5-epi-cytoxazone

An interesting protocol for stereoselective synthesis of (?)-cytoxazone and its unnatural stereoisomer (+)-5-epi-cytoxazone from d-4-hydroxyphenylglycine in overall yields of 10% and 16%, respectively, is described. The stereoselective addition of cyanide

Stereoselective synthesis of oxazolidin-2-ones via an asymmetric aldol/curtius reaction: Concise total synthesis of (?)-cytoxazone

Herein, we are reporting an efficient approach toward the synthesis of 4,5-disubstituted oxazolidin-2-one scaffolds. The developed approach is based on a combination of an asymmetric aldol and a modified Curtius protocol, which uses an effective intramolecular ring closure to rapidly access a range of oxazolidin-2-one building blocks. This strategy also permits a straightforward and concise asymmetric total synthesis of (?)-cytoxazone. Consisting of three steps, this is one of the shortest syntheses reported to date. Ultimately, this convenient platform would provide a promising method for the early phases of drug discovery.

Preparation method of Cytoxazone and intermediate thereof

The invention discloses a preparation method of Cytoxazone and an intermediate of Cytoxazone. The preparation method disclosed by the invention comprises the following step: in a solvent, carrying outa salifying reaction shown in the specification on p-methoxyepoxy cinnamic acid and a resolving agent S-phenylethylamine to obtain the compounds shown in the formulas I and I' (See the specificationfor reference). By adopting the preparation method disclosed by the invention, Cytoxazone with relatively high yield and relatively high purity can be simply and efficiently obtained.

New approach for the stereoselective synthesis of (+)-epi-cytoxazone

The stereoselective total synthesis of (+)-epi-cytoxazone was performed satisfactorily in 8 steps, in 17percent overall yield, via a novel route from 2,3-O-(3-pentylidene)-(R)-glyceraldehyde. The bulky group alkene-ketal allowed intramolecular control of

Diastereoselective Radical Couplings Enable the Asymmetric Synthesis of anti-β-Amino-α-hydroxy Carboxylic Acid Derivatives

anti-β-Amino-α-(aminoxy) esters or amides are synthesized by merging polar asymmetric aza-Michael additions of lithium 1-phenylethylamides to α,β-unsaturated carboxylic acid derivatives and diastereoselective radical couplings with the persistent free rad