143527-70-2

Basic information

• Product Name: (4S,5R)-3-(tert-Butoxycarbonyl)-2,2-dimethyl-4-phenyloxazolidine-5-carboxylic acid
• Synonyms: (4s-trans)-2,2-dimethyl-4-phenyl-3,5-oxazolidinedicarboxylic acid 3-(1,1-dimethylethyl) ester;(4S,5R)-3,5-OXAZOLIDINEDICARBOXYLIC ACID-2,2-DIMETHYL-4-PHENYL-3-(1,1-DIMETHYLETHYL)ESTER;(4S,5R)-3,5-Oxazolidinedicarbo;(4S,5R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-4-phenyloxazolidine-5-carboxylic;(4S,5R)-3-(N-tert-butoxycarbonyl)-2,2-dimethyl-4-phenyloxazolidine-5-carboxylic acid;(4S,5R)-3,5-OXAZOLIDINEDICARBOXYLIC ACID, 2,2-DIMETHYL-4-PHENYL-3-(1,1-DIMETHYLETHYL)ESTER,99%;(4S,5R)-2,2-Dimethyl-4-phenyl-3,5-oxazolidinedicarboxylic Acid 3-(1,1- Dimethylethyl) Ester;3,5-Oxazolidinedicarboxylic acid, 2,2-dimethyl-4-phenyl-, 3-(1,1-dimethylethyl) ester, (4S,5R)-
• CAS NO: 143527-70-2
• Molecular Formula: C₁₇H₂₃NO₅
• Molecular Weight: 321.37
• EINECS: 1806241-263-5
• Product Categories: Various Intermediates;Intermediates;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 143527-70-2.mol
• Article Data: 7

Chemical Properties

• Melting Point: 112.0 to 116.0 °C
• Boiling Point: 459.009 °C at 760 mmHg
• Flash Point: 231.4 °C
• Appearance: off-white semi solid
• Density: 1.177
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.526
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), DMSO (Slightly), Ethyl Acetate (Slightly)
• PKA: 3.11±0.60(Predicted)
• 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(143527-70-2)
• EPA Substance Registry System: (4S,5R)-3-(tert-Butoxycarbonyl)-2,2-dimethyl-4-phenyloxazolidine-5-carboxylic acid(143527-70-2)

Safety Data

• Hazardous Substances Data: 143527-70-2(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Semi Solid

InChI:InChI=1/C17H23NO5/c1-16(2,3)23-15(21)18-12(11-9-7-6-8-10-11)13(14(19)20)22-17(18,4)5/h6-10,12-13H,1-5H3,(H,19,20)/t12-,13+/m0/s1

Upstream product

• 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 
• 143527-75-7 (2R,3S) ethyl N-(t-butoxycarbonyl)-3-phenylisoserine 
• 126060-73-9 ethyl (2R,3R)-3-phenyl-2,3-oxiranepropanoate 
• 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 
• 147058-27-3 methyl (2R,3S)-2-hydroxy-3-phenyl-3-<(S)-1-methylbenzylamino>propanoate 
• 157240-36-3 (2R,3S)-3-phenylisoserine methyl ester 
• 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 

Downstream Products

• 679825-65-1 5-(4-oxo-1-adamantyl) 3-tert-butyl (4S,5R)-2,2-dimethyl-4-phenyl-1,3-oxazolidine-3,5-dicarboxylate 
• 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 
• 163513-94-8 13-O-(((4S,5R)-3-(tert-Butoxycarbonyl)-2,2-dimethyl-4-phenyloxazolidin-5-yl)carbonyl)-4-deacetyl-7-(triethylsilyl)-13-epi-baccatin III 
• 159262-93-8 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.

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.

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.