496877-70-4

Basic information

• Product Name: 2-Oxazolidinone, 5,5-dimethyl-3-[(phenylmethoxy)acetyl]-4-(phenylmethyl)-, (4S)-
• Synonyms: (S)-4-benzyl-2-(2'-benzyloxyacetyl)-5,5-dimethyloxazolidin-2-one;(S)-4-Benzyl-3-(2-benzyloxy-acetyl)-5,5-dimethyl-oxazolidin-2-one
• CAS NO: 496877-70-4
• Molecular Formula: C21H23NO4
• Molecular Weight: 353.41200
• Mol File: 496877-70-4.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 501.4±33.0 °C(Predicted)
• Density: 1.182±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 2-Oxazolidinone, 5,5-dimethyl-3-[(phenylmethoxy)acetyl]-4-(phenylmethyl)-, (4S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Oxazolidinone, 5,5-dimethyl-3-[(phenylmethoxy)acetyl]-4-(phenylmethyl)-, (4S)-(496877-70-4)
• EPA Substance Registry System: 2-Oxazolidinone, 5,5-dimethyl-3-[(phenylmethoxy)acetyl]-4-(phenylmethyl)-, (4S)-(496877-70-4)

Safety Data

• Hazardous Substances Data: 496877-70-4(Hazardous Substances Data)

Upstream product

• 19810-31-2 Benzyloxyacetyl chloride 
• 168297-85-6 (S)-4-benzyl-5,5-dimethyloxazolidin-2-one 

Downstream Products

• 768391-61-3 (2'S,3'S,4S)-4-benzyl-3-(2'-benzyloxy-3'-(furan-2-yl)-3'-hydroxypropionyl)-5,5-dimethyloxazolidin-2-one 
• 846542-11-8 (2'S,3'R,4S,4'R,5'R)-4-benzyl-3-[2',4',6'-tris(benzyloxy)-5'-(tert-butyldimethylsilanyloxy)-3'-hydroxyhexanoyl]-5,5-dimethyloxazolidin-2-one 
• 846542-12-9 (2'S,3'S,4S,4'R,5'R)-4-benzyl-3-[2',4',6'-tris(benzyloxy)-5'-(tert-butyldimethylsilanyloxy)-3'-hydroxyhexanoyl]-5,5-dimethyloxazolidin-2-one 
• 768391-58-8 (2'S,3'R,4S)-4-benzyl-3-(2'-benzyloxy-3'-hydroxy-5'-hexanoyl)-5,5-dimethyloxazolidin-2-one 
• 768391-57-7 (S)-4-Benzyl-3-((2S,3R)-2-benzyloxy-3-hydroxy-4-methyl-pentanoyl)-5,5-dimethyl-oxazolidin-2-one 
• 768391-60-2 (2'S,3'R,4S)-4-benzyl-3-(2'-benzyloxy-3'-hydroxy-3'-(4''-nitrophenyl)propionyl)-5,5-dimethyloxazolidin-2-one 
• 496877-73-7 (S)-4-Benzyl-3-[(2S,3R)-2,4-bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-butyl]-5,5-dimethyl-oxazolidin-2-one 
• 768392-11-6 (S)-4-Benzyl-3-[(1S,2S,3R)-2-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-3-(4-nitro-phenyl)-propyl]-5,5-dimethyl-oxazolidin-2-one 
• 768392-05-8 (2'S,3'R,4S)-4-benzyl-3-[2'-benzyloxy-3'-(tert-butyldimethylsilanyloxy)-3'-(4''-nitrophenyl)propionyl]-5,5-dimethyloxazolidin-2-one 
• 768392-07-0 (1'S,2'S,3'R,4S)-4-benzyl-3-(2-benzyloxy-3-(tert-butyldimethylsilanyloxy)-1-hydroxyoctyl)-5,5-dimethyloxazolidin-2-one 
• 768392-09-2 (1'S,2'S,3'R,4S)-4-benzyl-3-[2-benzyloxy-3-(triethylsilanyloxy)-1-hydroxy-5-methylhexyl]-5,5-dimethyloxazolidin-2-one 
• 768392-01-4 (2'S,3'R,4S)-4-benzyl-3-(2'-benzyloxy-3'-(tert-butyldimethylsilanyloxy)octanoyl)-5,5-dimethyloxazolidin-2-one 
• 768392-03-6 (2'S,3'R,4S)-4-benzyl-3-(2-benzyloxy-5-methyl-3-triethylsilanyloxyhexanoyl)-5,5-dimethyloxazolidin-2-one 
• 768392-12-7 (S)-4-Benzyl-3-[(1S,2S,3S)-2-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-3-furan-2-yl-1-hydroxy-propyl]-5,5-dimethyl-oxazolidin-2-one 

Relevant articles and documents

N-α-Benzyloxyacetyl derivatives of (S)-4-benzyl-5,5- dimethyloxazolidin-2-one for the asymmetric synthesis of differentially protected α,β-dihydroxyaldehydes

α-Dibenzylamino- and α-benzyloxy- derivatives of N-acetyl-(S)-4-benzyl-5,5-dimethyloxazolidin-2-one readily undergo highly stereoselective boron mediated syn-aldol reactions with a range of aromatic and aliphatic aldehydes, generating the syn-aldol products in good to excellent yields as single diastereoisomers after purification. In the α-dibenzylamino series, deprotection of the functionalised aldol fragments to the corresponding α-amino-β-hydroxy methyl ester or α-amino-β-hydroxyaldehyde proved problematic, with a range of N- and O-protecting groups giving mixtures of products arising from endocyclic and exocyclic cleavage pathways. However, in the α-benzyloxy series, O-silyl protection of the aldol products, and subsequent DIBAL reduction gives stereoselectively the corresponding N-1′-hydroxyalkyloxazolidin-2-ones, which undergo base promoted fragmentation to the desired highly functionalised and differentially protected α,β-dihydroxyaldehydes in good yields and without loss of stereochemical integrity.