857637-92-4

Basic information

• Product Name: (4S,5R)-(-)-4-Benzyl-5-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)-2-oxazolidinone,99%
• Synonyms: (4S,5R)-(-)-4-Benzyl-5-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)-2-oxazolidinone,99%;(4S,5R)-(-)-4-Benzyl-5-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)-2-oxazolidinone, 99%;(4S,5R)-(-)-4-Benzyl-5-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl-2-oxazolidinone, 99%;(4S,5R)-4-benzyl-5-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)-1,3-oxazolidin-2-one
• CAS NO: 857637-92-4
• Molecular Formula: C₁₈H₁₄F₁₃NO₂
• Molecular Weight: 523.29
• Product Categories: organic amine
• Mol File: 857637-92-4.mol
• Article Data: 3

Chemical Properties

• Melting Point: 90-95°C
• Boiling Point: 421.8±40.0 °C(Predicted)
• Appearance: white/Powder
• Density: 1.460±0.06 g/cm3(Predicted)
• PKA: 12.58±0.60(Predicted)
• CAS DataBase Reference: (4S,5R)-(-)-4-Benzyl-5-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)-2-oxazolidinone,99%(CAS DataBase Reference)
• NIST Chemistry Reference: (4S,5R)-(-)-4-Benzyl-5-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)-2-oxazolidinone,99%(857637-92-4)
• EPA Substance Registry System: (4S,5R)-(-)-4-Benzyl-5-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)-2-oxazolidinone,99%(857637-92-4)

Safety Data

• Hazardous Substances Data: 857637-92-4(Hazardous Substances Data)

Usage

Reaction

A chiral fluorous support for conventional and high-throughput organic synthesis. Induces high stereoselectivity in aldol reactions, cycloadditions, conjugate additions and a variety of other reactions of N-acyl derivatives. The fluorous chain permits rapid and efficient isolation of products by solid phase extraction, using only minimal amounts of common solvents.Class of catalytic ligands which when used with a reducing agent, exhibit enantioselectivity in the reduction of a wide range of substrates.

Upstream product

• 91084-05-8 methyl (S)-2-ethyloxycarbonylamino-3-phenylpropanoate 
• 114744-85-3 [(S)-1-(methoxy-methyl-carbamoyl)-2-phenyl-ethyl]-carbamic acid benzyl ester 
• 2043-57-4 1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-8-iodooctane 
• 871210-05-8 2(S)-(benzyloxycarbonylamino)-6,6,7,7,8,8,9,9,10,10,11,11,11-tridecafluoro-1-phenyl-undecan-3-one 
• 871210-04-7 2(S)-(iso-propoxycarbonylamino)-6,6,7,7,8,8,9,9,10,10,11,11,11-tridecafluoro-1-phenyl-undecan-3-one 
• 19887-32-2 (ethoxycarbonyl)-L-phenylalanine 
• 63-91-2 L-phenylalanine 
• 857637-83-3 (E)-(4S,5R)-4-benzyl-3-(3'-phenyl-2'-propenoyl)-5-(1'H,1'H,2'H,2'H-perfluorooctyl)-2-oxazolidinone 
• 857637-84-4 (E)-(4S,5R)-4-benzyl-3-(3'-ethoxycarbonyl-2'-propenoyl)-5-(1'H,1'H,2'H,2'H-perfluorooctyl)-2-oxazolidinone 
• 871210-02-5 2(S)-(ethoxycarbonylamino)-6,6,7,7,8,8,9,9,10,10,11,11,11-tridecafluoro-1-phenyl-undecan-3-one 
• 190378-46-2 2(S)-N-(ethyloxycarbonyl)-N'-methoxy-N'-methylphenylalaninamide 
• 857637-81-1 (E)-(4S,5R)-4-benzyl-3-(2'-butenoyl)-5-(1'H,1'H,2'H,2'H-perfluorooctyl)-2-oxazolidinone 
• 857637-87-7 (3'R,4S,5R)-4-benzyl-3-(3'-ethoxycarbonyl-4'-methyl-pentanoyl)-5-(1'H,1'H,2'H,2'H-perfluorooctyl)-2-oxazolidinone 
• 857637-86-6 (3'R,4S,5R)-4-benzyl-3-(4'-methyl-3'-phenyl-pentanoyl)-5-(1'H,1'H,2'H,2'H-perfluorooctyl)-2-oxazolidinone 

Downstream Products

• 857637-81-1 (E)-(4S,5R)-4-benzyl-3-(2'-butenoyl)-5-(1'H,1'H,2'H,2'H-perfluorooctyl)-2-oxazolidinone 
• 857637-85-5 (3'R,4S,5R)-4-benzyl-3-(3',4'-dimethyl-pentanoyl)-5-(1'H,1'H,2'H,2'H-perfluorooctyl)-2-oxazolidinone 
• 857637-86-6 (3'R,4S,5R)-4-benzyl-3-(4'-methyl-3'-phenyl-pentanoyl)-5-(1'H,1'H,2'H,2'H-perfluorooctyl)-2-oxazolidinone 
• 857637-87-7 (3'R,4S,5R)-4-benzyl-3-(3'-ethoxycarbonyl-4'-methyl-pentanoyl)-5-(1'H,1'H,2'H,2'H-perfluorooctyl)-2-oxazolidinone 
• 864072-74-2 (3'R,4S,4'S,5R,5'R)-4-benzyl-3-((5'-methyl-2',3'diphenylisoxazolidin-4'-yl)carbonyl)-5-(1'H,1'H,2'H,2'H-perfluorooctyl)-2-oxazolidinone 
• 857637-83-3 (E)-(4S,5R)-4-benzyl-3-(3'-phenyl-2'-propenoyl)-5-(1'H,1'H,2'H,2'H-perfluorooctyl)-2-oxazolidinone 
• 857637-84-4 (E)-(4S,5R)-4-benzyl-3-(3'-ethoxycarbonyl-2'-propenoyl)-5-(1'H,1'H,2'H,2'H-perfluorooctyl)-2-oxazolidinone 

Relevant articles and documents

FLUOROUS OXAZOLIDINONE CHIRAL AUXILIARY COMPOUNDS AND METHODS OF MANUFACTURE

The present invention relates generally to perfluoroalkyl chiral auxiliary compounds and methods of manufacture. These compounds have the functionality to effectively support the synthesis of chiral compounds in single reactions, high-throughput parallel recations, or combinatorial reactions The invention relates to two oxazolidmone chiral auxiliaries (1) and (2): wherein Rf is a perfluoroalkyl group having the general formula (CH2)x-CyF2y+1 where x = 1-5 and y = 4-10 and wherein B is an unfunctionalized aryl, alkyl or arylalkyl group Pn a preferred embodiment, x = 2 and y = 6 and B is derived from unfunctionalized ammo acids The ammo acids may be from either the D- or L- series, and are preferably enantiomeπcally pure or in very high enantiomeric excess in either configuration.

Stereoselective conjugate radical additions: Application of a fluorous oxazolidinone chiral auxiliary for efficient tin removal

(Chemical Equation Presented) A series of asymmetric free-radical-mediated intermolecular conjugate additions using a fluorous oxazolidinone chiral auxiliary has been completed. The fluorous auxiliary facilitated product isolation using fluorous solid phase extractions (FSPE), effectively removing excess organic and organometallic reagents. Parallel reactions carried out with a similar but nonfluorous norephedrine-derived oxazolidinone demonstrated the superior stereoselectivity and purification obtainable with the fluorous chiral auxiliary.