218439-10-2

Basic information

• Product Name: 3-((4S)-4-phenylmethyl-2-oxazolidinoyl)carbonylmethylenetriphenylphosphorane
• Synonyms: 3-((4S)-4-phenylmethyl-2-oxazolidinoyl)carbonylmethylenetriphenylphosphorane
• CAS NO: 218439-10-2
• Molecular Weight: 479.515
• Mol File: 218439-10-2.mol

Chemical Properties

• CAS DataBase Reference: 3-((4S)-4-phenylmethyl-2-oxazolidinoyl)carbonylmethylenetriphenylphosphorane(CAS DataBase Reference)
• NIST Chemistry Reference: 3-((4S)-4-phenylmethyl-2-oxazolidinoyl)carbonylmethylenetriphenylphosphorane(218439-10-2)
• EPA Substance Registry System: 3-((4S)-4-phenylmethyl-2-oxazolidinoyl)carbonylmethylenetriphenylphosphorane(218439-10-2)

Safety Data

• Hazardous Substances Data: 218439-10-2(Hazardous Substances Data)

Upstream product

• 90719-32-7 (S)-4-Benzyl-2-oxazolidinone 
• 104324-16-5 (4S)-(+)-3-(chloroacetyl)-4-(phenylmethyl)-2-oxazolidinone 
• 603-35-0 triphenylphosphine 
• 129549-13-9 4S-3-(2-bromoacetyl)-4-(phenylmethyl)-2-oxazolidinone 
• 139278-12-9 (4S)-4-benzyl-3-<2-(triphenylphosphonio)acetyl>-2-oxazolidinone bromide 

Downstream Products

• 174003-89-5 (4S)-3-<(E)-4'bromo-4',4'-difluoro-2'-butanoyl>-4-benzyl-2-oxazolidinone 
• 174003-91-9 (2R,1'R,2'R,4S)-ethyl N-diphenylmethylidene-2-<2'-<(4-benzyl-2-oxazolidinon-3-yl)carbonyl>-3',3'-difluoro>cyclopropylglycinate 
• 218439-16-8 (S)-4-Benzyl-3-[(2S,4S)-4-(tert-butyl-dimethyl-silanyloxy)-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methyl-butyryl]-oxazolidin-2-one 
• 218439-38-4 (S)-4-Benzyl-3-[(S)-4-(tert-butyl-dimethyl-silanyloxy)-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-butyryl]-oxazolidin-2-one 
• 922174-49-0 (4S,2'S,6'S)-3-(2',6'-dimethyl-7'-carboxyheptanoyl)-4-phenylmethyl-1,3-oxazolidin-2-one 
• 922174-48-9 (4S,2'S,6'R)-3-(2',6'-dimethyl-7'-carboxyheptanoyl)-4-phenylmethyl-1,3-oxazolidin-2-one 
• 922174-45-6 (4S,2'S,6'S)-3-[2',6'-dimethyl-8'-(tetrahydro-2H-pyran-2-yloxy)octanoyl]-4-phenylmethyl-1,3-oxazolidin-2-one 
• 922174-44-5 (4S,2'S,6'R)-3-[2',6'-dimethyl-8'-(tetrahydro-2H-pyran-2-yloxy)octanoyl]-4-phenylmethyl-1,3-oxazolidin-2-one 
• 922174-42-3 (4S,6'S)-3-[6'-methyl-8'-(tetrahydro-2H-pyran-2-yloxy)octanoyl]-4-phenylmethyl-1,3-oxazolidin-2-one 
• 922174-40-1 (4S,6'R)-3-[6'-methyl-8'-(tetrahydro-2H-pyran-2-yloxy)octanoyl]-4-phenylmethyl-1,3-oxazolidin-2-one 
• 505093-89-0 (4S)-3-[cis-(4-t-butoxycarbonylaminocyclohexyl)propenoyl]-4-phenylmethyl-2-oxazolidinone 
• 505093-89-0 (4S)-3-[trans-(4-t-butoxycarbonylaminocyclohexyl)propenoyl]-4-phenylmethyl-2-oxazolidinone 

Relevant articles and documents

Stereoselective Visible-Light Catalyzed Cyclization of Bis(enones): A Viable Approach to the Synthesis of Enantiomerically Enriched Cyclopentane Rings

Photoredox catalytic cyclization of aryl enones in the presence of visible light, promoted either by metals or organic dyes, represent a valuable strategy for the synthesis of cycloalkanes. The development of a stereoselective version of such transformation, in the presence of the metal-free catalyst Eosin Y was studied, with the aim to realize an efficient protocol for the in-flow synthesis of enantiomerically enriched functionalized cyclopentane rings, taking advantage of the flow reactors technology. The use of a chiral auxiliary on the bisenone to be cyclized offers a straightforward and convenient option to exert a stereocontrol on the light-driven cyclization. By exploiting Evans’ oxazolidinones, the stereoselective light-driven cyclization affords, after the removal of the chiral auxiliary, a functionalized 1,2-trans cyclopentane ring in up to 83/17 enantiomeric ratio. When the reaction was performed in continuo, in a homemade coil photoreactor, high yields were observed. The cyclization was also successfully realized in a 3D-printed mesoreactor, without any change in the diastereoseletctivity of the process.

Total synthesis and absolute configuration of radiosumin, a strong trypsin inhibitor from the blue-green alga Plectonema radiosum

Radiosumin (1), a strong trypsin inhibitory dipeptide isolated from the freshwater blue-green alga Plectonema radiosum (NIES-515), was synthesized for the first time by use of the hetero Diels-Alder reaction, the Horner-Wadsworth-Emmons reaction, the Corey-Winter reaction, regioselective hydrogenation, and reduction with zinc and formic acid as key steps, which unambiguously determined the absolute configuration of the structurally unique and biologically intriguing aquatic natural product (1).

A highly diastereoselective synthesis of trans-3,4-(difluoromethano)glutamic acid

Reaction of enantiomerically pure N-(4'-bromo-4',4'-difluorocrotonoyl)oxazolidinone 5 with lithium enolate of N-diphenylmethylideneglycinate 6 in DMF proceeded in highly diastereoselective manner to give trans-disubstituted gem-difluorocyclopropane 7, which was readily converted to the 3,4-(difluoromethano)glutamic acid 4.

A rapid access to both enantiomers of 1,2,3,4-tetranor B-trienic 18,18,18-trifluorosteroids. The first enantiocontrolled total synthesis of 18,18,18-trifluorosteroids

Chiral A-tetranor B-trienic 18,18,18-trifluorosteroid 2a and its enantiomer 1a were synthesised by the thermolysis of chiral olefinic benzocyclobutenes 7b and 7a which were in turn prepared by the aldol reaction of chiral oxazolidinone 5 and 11 with 2-(4-