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

• 871210-16-1 (2S,3R)-2-(iso-propoxycarbonylamino)-6,6,7,7,8,8,9,9,10,10,11,11,11-tridecafluoro-1-phenyl-undecan-3-ol 
• 871210-15-0 (2S,3R)-2-(ethoxycarbonylamino)-6,6,7,7,8,8,9,9,10,10,11,11,11-tridecafluoro-1-phenyl-undecan-3-ol 
• 871210-17-2 (2S,3R)-2-(benzyloxycarbonylamino)-6,6,7,7,8,8,9,9,10,10,11,11,11-tridecafluoro-1-phenyl-undecan-3-ol 
• 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 
• 857637-81-1 (E)-(4S,5R)-4-benzyl-3-(2'-butenoyl)-5-(1'H,1'H,2'H,2'H-perfluorooctyl)-2-oxazolidinone 
• 190378-46-2 2(S)-N-(ethyloxycarbonyl)-N'-methoxy-N'-methylphenylalaninamide 
• 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 
• 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 
• 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 
• 63-91-2 L-phenylalanine 
• 19887-32-2 (ethoxycarbonyl)-L-phenylalanine 
• 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 

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 
• 857637-84-4 (E)-(4S,5R)-4-benzyl-3-(3'-ethoxycarbonyl-2'-propenoyl)-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 
• 857637-85-5 (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 

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.

Practical synthesis of fluorous oxazolidinone chiral auxiliaries from α-amino acids

A series of new fluorous-supported oxazolidinone chiral auxiliaries has been prepared using a versatile and general five-step pathway, starting from readily available chiral α-amino acids. The key feature of this synthesis is the efficient generation of a suitably active perfluoroalkyllithium species. By use of this protocol, the auxiliaries can be obtained in high enantiomeric purity and on multigram scales from L-phenylalanine and L-valine with overall yields as high as 55%. The new methodology also incorporates fluorous solid-phase extraction on the large scale, allowing bulk quantities (up to 25 g) of fluorous compounds to be purified from the crude reaction mixture.