147058-27-3

Upstream product

• 69350-13-6 N-benzylidene-(S)-α-methylbenzylamine 
• 150811-50-0 (E)-((2-((tert-butyldimethylsilyl)oxy)-1-methoxyvinyl)oxy)trimethylsilane 
• 212764-79-9 methyl (2R,3S)-2-methoxy-3-phenyl-3-<(S)-methylbenzylamino>propanoate 
• 1310-73-2 sodium hydroxide 
• 154306-81-7 (3R,4S)-3-hydroxy-4-phenyl-1-<(S)-methylbenzyl>azetidin-2-one 
• 67-56-1 methanol 
• 1254191-15-5 C₂₅H₃₃NO₅ 

Downstream Products

• 32981-85-4 methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate 
• 153652-71-2 (4S,5R)-2,2-Dimethyl-4-phenyl-oxazolidine-3,5-dicarboxylic acid 3-tert-butyl ester 5-methyl ester 
• 143615-03-6 (4S,5R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-4-phenyloxazolidine-5-carboxylic acid 
• 124605-42-1 methyl (2R,3S)-3-(tert-butoxycarbonylamino)-2-hydroxy-3-phenylpropionate 
• 157240-36-3 (2R,3S)-3-phenylisoserine methyl ester 

Relevant academic research and scientific papers

A highly diastereoselective synthesis of α-hydroxy-β-amino acid derivatives via a Lewis acid catalyzed three-component condensation reaction

A very efficient three-component synthesis of a series of syn α-hydroxy-β-amino esters, obtained in high diastereoselection and yield, was realized starting from an aldehyde, benzylamine, and the ketene silyl acetals derived from Ley's lactones. The synthetic protocol was optimized and the above compounds were obtained without the isolation of intermediates. The origin of the observed diastereoselection was investigated through a computational model of the key reaction step.

Asymmetric synthesis of β-amino-α-hydroxy acids through Lewis acid-mediated addition of ketene acetal to imines

Asymmetric synthesis of β-amino-α-hydroxy acids, key components of medicinally important molecules including Paclitaxel, KRI-1314, amastatin, and microginin, has been attained from the aldimine coupling of chiral imines N-alkylidene-(S)- or (R)-α-methylbenzylamine with (Z)-α-methoxyketene methyltrimethylsilyl acetal, followed by demethylation, hydrogenolysis, and hydrolysis.

Practical synthesis of taxol side chain

Practical large scale synthesis of N-benzoyl-(2R,3S)-phenylisoserine methyl ester of the Taxol side chain has been attained from the coupling of chiral imine of N-[(S)-methylbenzyl]benzaldimine with (Z)-α-methoxy trimethylsilyl ketene acetal followed by the sequential reactions of lactamization, demethylation, methanolysis and N-benzoylation.

Process for the preparation of β-phenylisoserine and its analogues

This invention relates to a method for preparing β-phenylisoserine and analogues thereof having general formula (I) STR1 from an aromatic aldehyde and an α-methylarylamine-S, and through a lactam of general formula (II) as described herein. The acids of g

Method for the preparation of β-phenylisoserine derivatives

Method for the preparation of β-phenylisoserine derivatives of general formula (I) involving the action of an anhydride and hydrogen with a product of general formula (II). The products of general formula (I) are especially useful in the preparation of taxoids having outstanding antitumour properties. In general formulae (I) and (II), Ar is an aryl radical, Ph is a phenyl radical or an optionally substituted α or β-naphtyl, R is a hydrogen atom or an alkyl radical optionally substituted by a phenyl radical and R1 is an optionally substituted phenyl radical or a R2 --O radical wherein R2 is an alkyl, alkenyl, cycloalkyl, phenyl or heterocyclyl. STR1

Practical preparation of α-hydroxy-β-amino ester units; Stereoselective synthesis of taxol side chain and norstatine

An asymmetric reaction of chiral imines with α-silyloxy ketene acetals mediated by chiral boron reagents is described. The key to its success is the use of the chiral boron complex prepared in situ from (R)- or (S)-binaphthol and B(OPh)3. Both diastereomers of α-hydroxy-β-amino ester units are successfully prepared with high selectivities by the chiral boron reagents depending on the geometry of the silyl ketene acetals. The optically pure anti α-hydroxy-β-amino ester is obtained from (E)-silyl ketene acetal, while the corresponding syn α-hydroxy-β-amino ester is obtained from (Z)- silyl ketene acetal. The method can be efficiently applied to the stereoselective synthesis of taxol C-13 side chain and the norstatine family.

A Practical Access to Chiral Phenylisoserinates, Preparation of Taxotere Analogs

A practical diastereoselective synthesis of phenylisoserine methyl esters 8a-c is described using α-methyl-benzylamine as the chiral template of a Staudinger reaction.Optically pure diastereoisomers 6a-c were easily recovered by crystallization.After opening of these intermediate azetidinones by hydrochloric acid and methanol, regioselective cleavage of the chiral auxiliary was achieved by hydrogenation over palladium.Phenylisoserinates 8b,c were used to prepare analogs of Taxotere.