144541-45-7

Upstream product

• 67-56-1 methanol 
• 131968-73-5 Chloro-acetic acid (3S,4R)-1-benzoyl-2-oxo-4-phenyl-azetidin-3-yl ester 
• 131968-74-6 (2R,3S)-3-Amino-2-hydroxy-3-phenyl-propionic acid methyl ester 
• 98-88-4 benzoyl chloride 
• 780721-69-9 3-Amino-2-hydroxy-3-phenyl-propionic acid methyl ester 
• 55325-49-0 (±)-anti-3-amino-2-hydroxy-3-phenylpropanamide 
• 140196-38-9 1,1-dimethyl (2-oxo-1-phenylethyl)carbamate 
• 161060-38-4 [2-Hydroxy-2-(4-isopropyl-5-oxo-2,5-dihydro-oxazol-2-yl)-1-phenyl-ethyl]-carbamic acid tert-butyl ester 
• 55325-49-0 (2RS,3SR)-3-Phenylisoserinamide 
• 7309-55-9 N-benzoyl-(2R^*,3S^*)-3-phenylisoserine 
• 144494-74-6 (R)-3-benzamido-3-phenylpropanoic acid methyl ester 
• 186581-53-3 diazomethane 
• 195196-18-0 (3S,4S)-N-benzyl-4-hydroxy-3-phenylisoxazolidinone 
• 150949-07-8 methyl (2S,3S)-phenylisoserine 

Downstream Products

• 32981-85-4 methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate 
• 7309-55-9 N-benzoyl-(2R^*,3S^*)-3-phenylisoserine 
• 146848-91-1 (4S,5R)-2,4-diphenyl-2-oxazoline-5-carboxylic acid methyl ester 
• 132201-33-3 (2R,3S)-N-benzoyl-3-phenylisoserine 

Relevant academic research and scientific papers

Synthesis method of paclitaxel side chain and analogs thereof (by machine translation)

The invention discloses a synthesis method of a taxol side chain ((4S, 5R) -3 - benzoyl -2 - (4 - methoxyphenyl) -4 - phenyl -5 - oxazoline carboxylic acid) shown as a formula (f) and a series of reactions such as epoxidation, methyl esterification, ammonolysis, ester hydrolysis, condensation, configuration overturning, condensation and hydrolysis as well as analogues thereof. The invention discloses a synthesis method of the taxol side chain ((4S 5R) -3 -benzoyl -2 - (4 - methoxyphenyl) -4 - phenyl -5 - oxazoline carboxylic acid) and the like. The method has the advantages of short reaction time, high yield, good chiral selectivity, suitability for industrial production and the like. (by machine translation)

Preparation method of paclitaxel oxazole ring side chain intermediate

The invention provides a preparation method of a paclitaxel oxazole ring side chain intermediate, which can effectively enhance the single-step yield, thereby enhancing the total yield of the paclitaxel oxazole ring side chain and lowering the preparation cost. According to the method, suction filtration and concentration are directly carried out on a product (1) in a hydrogenation reduction stepin a process for synthesizing docetaxel by a four-step purification method, the product is used for a subsequent substitution reaction, and the product is subjected to a reaction in an organic solventwith a solvent polarity parameter of less than or equal to 4.5 to prepare a substitution product (2), so that the problem of low yield caused by incomplete extraction during hydrogenation reduction reaction post-treatment is solved.

Method for preparing optically active alpha-hydroxy-beta-amino acid compounds

The invention discloses a method for preparing optically active N-acyl-beta-hydroxy-amino ester compounds of formula II from alpha-acyloxy-beta-enamine ester compounds through a one-pot process. The method uses novel six-membered cyclic pyridinecarboxamid

Chemoselective esterification of α-hydroxyacids catalyzed by salicylaldehyde through induced intramolecularity

A new, direct and chemoselective esterification of α-hydroxyacids was developed using a reversible covalent-binding strategy. By taking advantage of acetal chemistry, simple aldehydes can be used to efficiently catalyze the esterification of α-hydroxy carboxylic acids in the presence of β-hydroxyacid moieties or other carboxylic acids in amounts equal to or in excess of the alcohols. A diverse array of α-aryl, α-alkyl, α-heteroaryl, and functionalized α-hydroxyacids were smoothly esterified with 1° and 2° alcohols catalyzed by 10 mol% inexpensive and commercially available salicylaldehyde, furnishing the resultant esterification products in 83-95% yields after a simple basic aqueous workup to remove the unreacted hydroxyacids. In addition, the salicylaldehyde can be recovered through vacuum distillation or silica gel purification, thereby meeting the standards of green chemistry. A mechanistic study proved that the formation of covalent adduct III during our proposed catalytic cycle (Scheme 1A) is responsible for the real catalysis.

Efficient enantioselective synthesis of α-hydroxy-β-amino acids using the Claisen and Curtius rearrangements

Highly enantioselective and facile synthesis of α-hydroxy-β- amino acids has been achieved using the Claisen and Curtius rearrangements as key reactions. Chiral allylic alcohols were employed, which can be prepared by asymmetric catalysis in both E- and Z

A practical diastereoselective synthesis of β-amino-α-hydroxy carboxylates

Practical synthetic routes to β-amino-α-hydroxy carboxylates (AHC) have been developed from amino acids. Reduction of β-amino-α- keto esters 6 with NaBH4 was found to give anti-AHCs 7 in high de, which were efficiently converted to the corresponding syn-AHCs 8 via oxazolidine ring 10 formation.

A practical and stereoselective synthesis of taxol side chain

Apractical and efficient synthesis of taxol C-13 side chain from cheap and easily available starting material is described.

Chemoenzymatic synthesis of the C-13 side chain of paclitaxel (Taxol) and docetaxel (Taxotere)

Reduction of methyl 3-chloro-2-oxo-3-phenylpropanoate with various reducing agents gave syn- and anti-3-chloro-2-hydroxy-3-phenylpropanoates 3, which underwent an efficient lipase-catalyzed resolution. All four diastereomers were subsequently converted to N-benzoyl-(2R,3S)-3-phenylisoserine methyl ester, C-13 side chain analogues of paclitaxel (Taxol).

Stereocontrolled Synthesis of the Taxol C-13 Side Chain: Methyl (2R,3S)-3-Benzoylamino-2-hydroxy-3-phenylpropanoate

Addition of lithiated methoxyallene 5 to literature-known amino aldehyde 3 followed by ozonolysis provided syn-configurated α-hydroxy-β-amino ester 6 in moderate overall yield and with an ee of 90%. The predominant formation of syn-compounds may be due to a chelate controlled addition step.

Totally stereocontrolled nitrone-ketene acetal based synthesis of (2S,3S)-N-benzoyl-and N-boc-phenylisoserine

A novel, nitrone-ketene acetal based approach to enantiopure (2S,3S)-N- benzoyl- and N-boc-phenylisoserine has been realized. The convergent approach, which involves the intermediacy of isoxazolidinones, proceeds in up to 59% overall yield and requires only three operations from the starting nitrones.