99773-54-3

Basic information

• Product Name: Oxiranecarboxaldehyde, 3-phenyl-, (2R,3R)-rel- (9CI)
• Synonyms: Oxiranecarboxaldehyde, 3-phenyl-, (2R,3R)-rel- (9CI)
• CAS NO: 99773-54-3
• Molecular Formula: C₉H₈O₂
• Molecular Weight: 148.15862
• Product Categories: ALDEHYDE
• Mol File: 99773-54-3.mol
• Article Data: 26

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Oxiranecarboxaldehyde, 3-phenyl-, (2R,3R)-rel- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Oxiranecarboxaldehyde, 3-phenyl-, (2R,3R)-rel- (9CI)(99773-54-3)
• EPA Substance Registry System: Oxiranecarboxaldehyde, 3-phenyl-, (2R,3R)-rel- (9CI)(99773-54-3)

Safety Data

• Hazardous Substances Data: 99773-54-3(Hazardous Substances Data)

Upstream product

• 14371-10-9 (E)-3-phenylpropenal 
• 21915-53-7 cis-2,3-epoxy-3-phenyl-1-propanol 
• 4510-34-3 (Z)-cinnamyl alcohol 
• 99773-42-9 2-Hydroxy-2-methyl-1-((2S,3S)-3-phenyl-oxiranyl)-propan-1-one 
• 99773-64-5 (1S,2R)-2-Bromo-1-hydroxy-4-methyl-1-phenyl-4-trimethylsilanyloxy-pentan-3-one 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 21915-53-7 2,3-epoxy-3-phenyl-1-propanol 
• 104-55-2 3-phenyl-propenal 
• 104196-23-8 (2S,3S)-2,3-epoxy-3-phenyl-1-propanol 
• 21915-53-7 (2R,3S)-(3-phenyloxiran-2-yl)methanol 
• 104-54-1 3-Phenylpropenol 
• 99773-42-9 2-Hydroxy-2-methyl-1-((2S,3R)-3-phenyl-oxiranyl)-propan-1-one 
• 76777-60-1 5-Hydroxy-5-phenyl-2-<(trimethylsilyl)oxy>-2-methyl-3-pentanone 
• 63677-96-3 (E)-2-hydroxy-2-methyl-5-phenylpent-4-en-3-one 

Downstream Products

• 40641-81-4 trans-2,3-epoxy-3-phenylpropan-1-ol 
• 53422-64-3 epoxy-3,4 phenyl-4 butyne-1 (trans) 
• 910484-84-3 2,2-difluoro-1-[(2S,3S)-3-phenyloxiranyl]-but-3-en-1-ol 
• 53422-64-3 (2SR,3RS)-3-ethynyl-2-phenyloxirane 
• 121534-31-4 3-[(3R,4R)-1-(2,4-Dimethoxy-benzyl)-2-oxo-4-((2R,3S)-3-phenyl-oxiranyl)-azetidin-3-yl]-4,5-diphenyl-3H-oxazol-2-one 
• 121534-31-4 3-[(3S,4S)-1-(2,4-Dimethoxy-benzyl)-2-oxo-4-((2R,3S)-3-phenyl-oxiranyl)-azetidin-3-yl]-4,5-diphenyl-3H-oxazol-2-one 
• 121534-32-5 [(3R,4R)-1-(2,4-Dimethoxy-benzyl)-2-oxo-4-((2R,3S)-3-phenyl-oxiranyl)-azetidin-3-yl]-carbamic acid benzyl ester 
• 121534-32-5 [(3S,4S)-1-(2,4-Dimethoxy-benzyl)-2-oxo-4-((2R,3S)-3-phenyl-oxiranyl)-azetidin-3-yl]-carbamic acid benzyl ester 
• 121534-30-3 2-[(3S,4S)-1-(2,4-Dimethoxy-benzyl)-2-oxo-4-((2R,3S)-3-phenyl-oxiranyl)-azetidin-3-yl]-isoindole-1,3-dione 
• 121534-33-6 [(3R,4R)-3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-2-oxo-4-((2R,3S)-3-phenyl-oxiranyl)-azetidin-1-yl]-acetic acid tert-butyl ester 

Relevant articles and documents

Borylation and rearrangement of alkynyloxiranes: A stereospecific route to substituted α-enynes

1,3-Enynes are important building blocks in organic synthesis and also constitute the key motif in various bioactive natural products and functional materials. However, synthetic approaches to stereodefined substituted 1,3-enynes remain a challenge, as they are limited to Wittig and cross-coupling reactions. Herein, stereodefined 1,3-enynes, including tetrasubstituted ones, were straightforwardly synthesized from cis or trans-alkynylated oxiranes in good to excellent yields by a one-pot cascade process. The procedure relies on oxirane deprotonation, borylation and a stereospecific rearrangement of the so-formed alkynyloxiranyl borates. This stereospecific process overall transfers the cis or trans-stereochemistry of the starting alkynyloxiranes to the resulting 1,3-enynes.

Highly Regio- and Stereodivergent Access to 1,2-Amino Alcohols or 1,4-Fluoro Alcohols by NHC-Catalyzed Ring Opening of Epoxy enals

Described is an unprecedented NHC-catalyzed (NHC=N-heterocyclic carbene), stereoselective ring opening of epoxy and cyclopropyl enals to deliver valuable compounds bearing multiple stereocenters. A straightforward three-step procedure involving two catalytic enantioselective transformations has been developed and leads to a regio- and stereodivergent synthesis of either 1,2-amino alcohols/diamines or 1,4-fluoro alcohols with excellent diastereo- and enantiopurity.

Diastereoselective synthesis of 3-acetoxy-4-(3-aryloxiran-2-yl)azetidin-2-ones and their transformation into 3,4-oxolane-fused bicyclic β-lactams

cis-3-Acetoxy-4-(3-aryloxiran-2-yl)azetidin-2-ones were prepared through a Staudinger [2+2]-cyclocondensation between acetoxyketene and the appropriate epoxyimines in a highly diastereoselective way. Subsequent potassium carbonate-mediated acetate hydrolysis, followed by intramolecular ring closure through epoxide ring opening, afforded stereodefined 3-aryl-4-hydroxy-2-oxa-6-azabicyclo[3.2.0]heptan-7-ones as a novel class of C-fused bicyclic β-lactams. Selective benzylic oxidation of bicyclic N-(4-methoxybenzyl)-β-lactams with potassium persulfate and potassium dihydrogen phosphate provided the corresponding N-aroyl derivatives as interesting leads for further β-lactamase inhibitor development.