87641-51-8

Basic information

• Product Name: (3S,4R)-3-<(1R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-4-<3-(p-nitrobenzyloxycarbonyl)-2-oxopropyl>azetidin-2-one
• Synonyms: (3S,4R)-3-<(1R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-4-<3-(p-nitrobenzyloxycarbonyl)-2-oxopropyl>azetidin-2-one
• CAS NO: 87641-51-8
• Molecular Weight: 464.591
• Mol File: 87641-51-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (3S,4R)-3-<(1R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-4-<3-(p-nitrobenzyloxycarbonyl)-2-oxopropyl>azetidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,4R)-3-<(1R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-4-<3-(p-nitrobenzyloxycarbonyl)-2-oxopropyl>azetidin-2-one(87641-51-8)
• EPA Substance Registry System: (3S,4R)-3-<(1R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-4-<3-(p-nitrobenzyloxycarbonyl)-2-oxopropyl>azetidin-2-one(87641-51-8)

Safety Data

• Hazardous Substances Data: 87641-51-8(Hazardous Substances Data)

Upstream product

• 102832-06-4 (3S,4R)-3-<(1R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-4-<<((4S)-4-ethyl-2-thioxo-1,3-thiazolidin-3-yl)carbonyl>methyl>azetidin-2-one 
• 78963-47-0 rac-3-{1-[(tert-Butyldimethylsilyl)oxy]ethyl}-4-acetoxyazetidin-2-one 
• 105995-50-4 magnesium 4-nitrobenzyl malonate 
• 88669-70-9 (3S,4R)-3-<(1R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-4-(carboxymethyl)azetidin-2-one 
• 77359-11-6 propanedioic acid mono[(4-nitrophenyl)methyl] ester 

Downstream Products

• 75321-07-2 (3S,4R)-3-[(R)-1-hydroxyethyl]-4-[3-(4-nitrobenzyl)-oxycarbonyl-2-oxopropyl]azetidin-2-one 

Relevant articles and documents

β-Lactams. 2. Diastereoselective Alkylative Discrimination of Racemic 3-Substituted 4-Acetoxyazetidin-2-ones and Its Application to the Synthesis of a Chiral Key Intermediate for Carbapenem Syntheses

Alkylation of rac 3-substituted 4-acetoxyazetidin-2-one 4 with chiral tin(II) enolate 8 derived from 3-acetyl-(4S)-ethyl-1,3-thiazolidine-2-thione (ETT) (7) proceeded in a highly diastereoselective manner to give alkylated products 9, 10, and 11 in 42percent, 20percent, and 9percent yields, respectively, after chromatographic purification.Similar alkylation of rac-5 with 8 gave 16, 17, and 18 in 45percent, 29percent, and 5percent yields, respectively.Compound 9 was readily converted to 33, a chiral key intermediate for the synthesis of carbapenems.Analytical separation of rac-4 was effectively done with an HPLC technique employing a chiral column packed with A(S)MBC.