850166-76-6

Upstream product

• 156324-98-0 [(R)-(Methoxy-methyl-carbamoyl)-(4-methoxy-phenyl)-methyl]-carbamic acid tert-butyl ester 
• 159848-74-5 1,1-dimethylethyl (R)-N-[2-hydroxy-1-(4-methoxyphenyl)-ethyl]carbamate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 22818-40-2 D-4-hydroxyphenylglycine 
• 57591-61-4 methyl (R)-2-amino-2-(4-hydroxyphenyl)acetate hydrochloride 
• 143323-49-3 (R)-methyl 2-((tert-butoxycarbonyl)amino)-2-(4-hydroxyphenyl)acetate 
• 193073-85-7 methyl (R)-2-((tert-butoxycarbonyl)amino)-2-(4-methoxyphenyl)acetate 
• 27460-85-1 N-(tert-butoxycarbonyl)-D-(4-hydroxyphenyl)glycine 
• 156324-97-9 [(R)-(4-Hydroxy-phenyl)-(methoxy-methyl-carbamoyl)-methyl]-carbamic acid tert-butyl ester 

Downstream Products

• 156324-99-1 (E)-(S)-4-tert-Butoxycarbonylamino-4-(4-methoxy-phenyl)-but-2-enoic acid ethyl ester 
• 635313-39-2 1,1-dimethylethyl (1R,2R)-N-[2-hydroxy-1-(4-methoxyphenyl)-3-butenyl]carbamate 
• 156407-80-6 Acetic acid (1R,2R)-2,3-diacetoxy-1-[(R)-tert-butoxycarbonylamino-(4-methoxy-phenyl)-methyl]-propyl ester 
• 156324-96-8 Acetic acid (1S,2S)-2,3-diacetoxy-1-[(R)-tert-butoxycarbonylamino-(4-methoxy-phenyl)-methyl]-propyl ester 
• 156325-00-7 [(E)-(S)-4-Hydroxy-1-(4-methoxy-phenyl)-but-2-enyl]-carbamic acid tert-butyl ester 
• 156325-03-0 [(Z)-(S)-4-Hydroxy-1-(4-methoxy-phenyl)-but-2-enyl]-carbamic acid tert-butyl ester 
• 156325-05-2 Phenyl-carbamic acid (2R,3S)-3-[(R)-tert-butoxycarbonylamino-(4-methoxy-phenyl)-methyl]-oxiranylmethyl ester 
• 156325-06-3 [(1R,2S)-2-Hydroxy-1-(4-methoxy-phenyl)-2-((S)-2-oxo-[1,3]dioxolan-4-yl)-ethyl]-carbamic acid tert-butyl ester 
• 156407-79-3 [(1R,2S,3S)-2,3,4-Trihydroxy-1-(4-methoxy-phenyl)-butyl]-carbamic acid tert-butyl ester 
• 156325-04-1 [(R)-((2S,3R)-3-Hydroxymethyl-oxiranyl)-(4-methoxy-phenyl)-methyl]-carbamic acid tert-butyl ester 
• 635313-43-8 2R-amino-1-(tert-butyldimethylsiloxy)methyl-2-(4-methoxyphenyl)-(1R)-ethyl 4-nitrobenzoate 
• 635313-42-7 3R-(tert-butoxycarbonyl)-amino-3-(4-methoxyphenyl)-2S-propane-1-(tert-butyl dimethylsiloxy)-2-ol 
• 700359-87-1 [3-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-1-(4-methoxy-phenyl)-propyl]-carbamic acid tert-butyl ester 
• 635313-40-5 (4R,5R)-5-(ethenyl)-4-(4-methoxyphenyl)-2-oxazolidinone 

Relevant academic research and scientific papers

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

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 (+)-5-epi-cytoxazone

A novel, stereo selective synthesis of (-)-cytoxazone 1a and stereoselective synthesis of (+)-5-epi-cytoxazone 1b were achieved via stereoselective Grignard addition of vinylmagnesium bromide on N-Boc aldehyde obtained from p-hydroxy-D-phenylglycine 2 followed by cyclization of N-Boc alcohol 6, ozonolysis and reduction to get (+)-5-epi-cytoxazone. Compound 6 underwent mitsunobu conditions, deprotection of ester followed by cyclization of N-Boc alcohol to get (-)-cytoxazone.

An Efficient Synthesis of Polyoxamic Acid Utilizing the Aryl Group as the Carboxyl Synthon. A New Approach to Polyhydroxyamino Acids.

Polyoxamic acid (1), an amino acid moiety of antifungal antibiotics polyoxins, has been efficiently synthesized from Boc-(R)-4-hydroxyphenylglycine (3) utilizing its aryl group as the carbonyl synthon.