153652-71-2

Usage

Uses

Used in Pharmaceutical Industry:
(4S,5R)-2,2-Dimethyl-4-phenyl-oxazolidine-3,5-dicarboxylic acid 3-tert-butyl ester 5-methyl ester is used as an intermediate for the synthesis of (4R,5S)-2,2-Dimethyl-4-phenyl-3,5-oxazolidinedicarboxylic Acid 3-(1,1-Dimethylethyl) Ester (O846295). (4S,5R)-2,2-Dimethyl-4-phenyl-oxazolidine-3,5-dicarboxylic acid 3-tert-butyl ester 5-methyl ester is a reagent for preparing 1,8-naphthyridine-3-carboxamide derivatives, which possess anticancer and anti-inflammatory activities.
Additionally, (4S,5R)-2,2-Dimethyl-4-phenyl-oxazolidine-3,5-dicarboxylic acid 3-tert-butyl ester 5-methyl ester can be used to synthesize taxol derivatives, which are known for their medical applications, particularly in the treatment of cancer.

Upstream product

• 124-41-4 sodium methylate 
• 174787-61-2 (4S,5S)-3-tert-butoxycarbonyl-2,2-dimethyl-4-phenyl-5-vinyloxazolidine 
• 145987-13-9 methyl (2S,3R)-2-acetoxy-3-bromo-3-phenylpropionate 
• 147058-27-3 methyl (2R,3S)-2-hydroxy-3-phenyl-3-<(S)-1-methylbenzylamino>propanoate 
• 157240-36-3 (2R,3S)-3-phenylisoserine methyl ester 
• 174787-57-6 (4S,5S)-5-(2-hydroxy)ethyl-4-phenyl-2-oxazolidinone 
• 174787-60-1 (4S,5S)-5-ethenyl-4-phenyl-1,3-oxazolidin-2-one 
• 100-58-3 phenylmagnesium bromide 
• 158341-43-6 methyl 2-acetoxy-3-azido-3-phenylpropanoate 
• 103-26-4 Methyl cinnamate 
• 122743-18-4 methyl (2R,3S)-2,3-dihydroxy-3-phenylpropanoate 
• 99458-15-8 Methyl (2R,3S)-(+)-2-hydroxy-3-azido-3-phenyl-propionate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 203806-61-5 (2R,3S)-3-tert-Butoxycarbonylamino-3-phenyl-2-triisopropylsilanyloxy-propionic acid methyl ester 

Downstream Products

• 203806-83-1 (4S,5R)-5-((S)-1-Hydroxy-but-3-enyl)-2,2-dimethyl-4-phenyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 163010-82-0 (4S,5R)-5-Formyl-2,2-dimethyl-4-phenyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 143615-03-6 (4S,5R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-4-phenyloxazolidine-5-carboxylic acid 

Relevant academic research and scientific papers

New approaches to the asymmetric synthesis of dipeptide isosteres via β-Lactam Synthon Method

New and efficient synthetic routes to dipeptide isosteres with high enantiomeric purity, e.g., hydroxyethylene, dihydroxyethylene and hydroxyethylamine isosteres, have been developed via oxiranes 6 and formyloxazolines 13 derived from N-t-Boc-β-lactams 4.

Synthesis of taxoids I. Regioselective Lewis acid-mediated ring-opening of aryl orthoacetates

The reaction of aryl orthoacetates with acetyl bromide readily proceeded regioselectively to afford the desirable aryl bromides in the presence of tin(II) or zinc bromide as a catalyst. The synthesis of some docetaxel derivatives is also described by using this improved process.

Synthetic application of chiral 4-methoxy-2-oxazolidinone synthons to 2-amino alcohols of biological interest

The versatility as chiral synthons of (4S, 5S)- and (4R, 5R)-5-allyl-4-methoxy-2-oxazolidinones, readily obtainable from 3-[(1S)-2-exo-alkoxy-1-apocamphanecarbonyl]-2-oxazolone, is demonstrated by the facile stereospecific conversions to (2R, 3S)-3-amino-2-hydroxy-3-phenylpentanoic acid, (2R, 3R, 5E, 7E)-2-amino-5,7-tetradecadien-3-ol and (2S, 3R)-dihydrosphingosine.

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.