143615-03-6

Basic information

• Product Name: (4S,5R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-4-phenyloxazolidine-5-carboxylic acid
• CAS NO: 143615-03-6
• Molecular Weight: 321.373
• Mol File: 143615-03-6.mol

Chemical Properties

• CAS DataBase Reference: (4S,5R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-4-phenyloxazolidine-5-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (4S,5R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-4-phenyloxazolidine-5-carboxylic acid(143615-03-6)
• EPA Substance Registry System: (4S,5R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-4-phenyloxazolidine-5-carboxylic acid(143615-03-6)

Safety Data

• Hazardous Substances Data: 143615-03-6(Hazardous Substances Data)

Upstream product

• 157240-36-3 (2R,3S)-3-phenylisoserine methyl ester 
• 147058-27-3 methyl (2R,3S)-2-hydroxy-3-phenyl-3-<(S)-1-methylbenzylamino>propanoate 
• 143527-74-6 ethyl (4S,5R)-3-tert-butoxycarbonyl-2,2-dimethyl-4-phenyl-5-oxazolidinecarboxylate 
• 144704-63-2 (4S,5R)-3-((2S,3R)-2-Bromo-3-hydroxy-3-phenyl-propionyl)-4-methyl-5-phenyl-oxazolidin-2-one 
• 100-52-7 benzaldehyde 
• 144787-20-2 (2R,3S)-3-azido-2-hydroxy-benzenepropanoic acid ethyl ester 
• 143615-00-3 (2R,3S)-3-amino-3-phenyl-2-hydroxypropionic acid ethyl ester 
• 154306-81-7 (3R,4S)-3-hydroxy-4-phenyl-1-<(S)-methylbenzyl>azetidin-2-one 
• 163010-80-8 2-<(4S,5R)-N-tert-butoxycarbonyl-2,2-dimethyl-4-phenyl-1,3-oxazolidin-5-yl>-1,3-thiazole 
• 174787-58-7 (4S,5S)-5-(2-methanesulfonyloxy)ethyl-4-phenyl-2-oxazolidinone 
• 174787-75-8 (4S,5S)-3-tert-butoxycarbonyl-4-phenyl-5-vinyl-2-oxazolidinone 
• 174787-61-2 (4S,5S)-3-tert-butoxycarbonyl-2,2-dimethyl-4-phenyl-5-vinyloxazolidine 
• 174787-59-8 (4S,5S)-5-(2-phenylselenenyl)ethyl-4-phenyl-2-oxazolidinone 
• 174787-57-6 (4S,5S)-5-(2-hydroxy)ethyl-4-phenyl-2-oxazolidinone 

Downstream Products

• 143527-76-8 4-acetoxy-2α-benzoyloxy-5β,20-epoxy-1-hydroxy-9-oxo-7β,10β-bis[(2,2,2-tri-chloroethoxy)carbonyloxy]-11-taxen-13α-yl (4S,5R)-3-tert-butoxycarbonyl-2,2-dimethyl-4-phenyl-5-oxazolidinecarboxylate 
• 159262-93-8 10-deacetylbaccatin III-13-O-[(4S,5R)-4-phenyl-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidine-5-carboxylate] 
• 204764-86-3 C₅₅H₇₄N₂O₁₃Si 
• 204764-87-4 C₅₆H₇₇NO₁₄Si 
• 204764-72-7 C₅₇H₇₉NO₁₅Si 
• 204991-77-5 C₆₁H₉₁NO₁₄Si₂ 
• 887781-23-9 tert-butyl (4S,5R)-2,2-dimethyl-5-(4,4-dimethyl-1-adamantylcarbonyloxy)-4-phenyloxazolidine-3-carboxylate 
• 170171-42-3 C₄₄H₄₉Cl₆NO₁₅ 
• 1082060-02-3 C₂₇H₃₇NO₅ 
• 912271-97-7 7,10-di(2,2,2-trichloroethyloxycarbonyl)-2-debenzoyl-2-(m-fluorobenzoyl)-10-deacetylbaccatin III-13-O-[(4S,5R)-4-phenyl-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidine-5-carboxylate] 
• 143527-73-5 C₅₁H₆₀Cl₃NO₁₇ 

Relevant articles and documents

PROCESS FOR PREPARING OXAZOLIDINE DERIVATIVES

A process for preparing (4S,5R)-5-carboxymethyl-2,2-dimethyl-4-phenyl-oxazolidine-3-carboxylic acid t-butyl ester, an intermediate in the preparation of anticancer compounds having a taxane skeleton, such as paclitaxel, docetaxol, etc.

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.

Process for preparing taxane derivatives, new derivatives obtained and pharmaceutical compositions containing them

A method for preparing taxane derivatives having general formula (I), novel derivatives thereby obtained and compositions containing same. In general formula (I), R is t.butoxy or phenyl, R1 is hydrogen or acetyl, and Ar is substituted phenyl or optionally substituted α or β-naphthyl. These novel taxane derivatives are useful as antileukemic and antitumoral agents. STR1

Synthesis of taxol and taxotere side chains by 2-(trimethylsilyl)thiazole based homologation of L-phenylglycine

L-Phenylglycine is homologated by the use of 2-(trimethylsilyl)thiazole into (2R,3S)-N-benzoyl- and N-tert-butoxycarbonyl-3-phenylisoserine, which are isolated as acetonide derivatives in 47 and 35% overall yields and with 84 and 90% ee, respectively.

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.

Improved protection and esterification of a precursor of the taxotere and taxol side chains

(4S,5R)-N-BOC-2,2-dimethyl-4-phenyl-5-oxazolidinecarboxylic acid 8 was prepared and efficiently esterified by conveniently protected baccatins 9a,b. Smooth deprotection in formic acid gave the N-deprotected intermediates of Taxotere and taxol. This protocol did not generate any epimerization at C-2′ and constitutes a pratical method to prepare Taxotere, taxol and analogs.