138332-40-8

Basic information

• Product Name: (3S,4R)-4-benzoylthio-3-<(1R)-(1-tert-butyldimethylsiloxy)ethyl>-azetidin-2-one
• Synonyms: (3S,4R)-4-benzoylthio-3-<(1R)-(1-tert-butyldimethylsiloxy)ethyl>-azetidin-2-one
• CAS NO: 138332-40-8
• Molecular Weight: 365.569
• Mol File: 138332-40-8.mol

Chemical Properties

• CAS DataBase Reference: (3S,4R)-4-benzoylthio-3-<(1R)-(1-tert-butyldimethylsiloxy)ethyl>-azetidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,4R)-4-benzoylthio-3-<(1R)-(1-tert-butyldimethylsiloxy)ethyl>-azetidin-2-one(138332-40-8)
• EPA Substance Registry System: (3S,4R)-4-benzoylthio-3-<(1R)-(1-tert-butyldimethylsiloxy)ethyl>-azetidin-2-one(138332-40-8)

Safety Data

• Hazardous Substances Data: 138332-40-8(Hazardous Substances Data)

Upstream product

• 134987-61-4 S-(trimethylsilyl)benzothioate 
• 144069-72-7 (3S,4R)-3-<(1R)-1-(tert-Butyldimethylsiloxy)ethyl>-4-phenylsulfinylazetidin-2-one 
• 98-91-9 thiobenzoic acid 
• 85281-73-8 (3S,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)-ethyl]-4-phenylthio-2-azetidinone 
• 76899-07-5 (3R,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one 
• 26144-40-1 Copper(I) thiobenzoate 

Downstream Products

• 164728-34-1 {(2R,3S)-2-Benzoylsulfanyl-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-1-yl}-oxo-acetic acid allyl ester 

Relevant articles and documents

Copper catalyzed process for producing 4-substituted azetidinone derivatives

A process for producing a 4-substituted azetidinone derivative represented by the following general formula ?III!: STR1 (wherein OR is a protected hydroxy group, Y is an alkyl group, an alkoxy group, a silyloxy group, a carbamoyloxy group, an amino group,

Structure-activity relationships of penem antibiotics: crystallographic structures and implications for their antimicrobial activities

Twelve closely related crystal structures of the penem derivatives revealed a characteristic short contact of the oxygen atom in the C2 side-chains with the S1 atom. The side-chain conformations of the crystal structures showed a good correlation with the antimicrobial activity. In particular, the penems which show high antimicrobial activity have similar torsion angles for S1-C2-C1'-C2', suggesting that the disposition of the C2' atom would be important for binding to penicillin-interacting enzymes. Two conformations of the C6 hydroxyethyl group were observed in the crystal structures. Of those two, the conformation with a larger torsion angle (δ = 179.2°) is deduced to be the enzyme-bound conformation in the Michaelis complex.

Copper-assisted substitution reaction for phenylthio group of a 4- phenylthioazetidinone derivative

The phenylthio group of 4-phenylthioazetidinone (1) was readily substituted with copper(I) salts of carboxylates, thiocarboxylates, and copper(I) enolates of malonates and β-ketoesters to give synthetic intermediates (3 and 4) for penem and carbapenem antibiotics.

An efficient synthesis of 4-heterofunction-substituted 3-(1-hydroxy)ethylazetidin-2-ones from 3-(1-hydroxy)ethyl-4-phenylsulfinylazetidin-2-one by reaction with silylated heteronucleophiles

3-(1-tert-Butyldimethylsiloxy)ethyl-4-sulfinylazetidin-2-one was reacted with silylated N-, S-, O-, and P-nucleophiles in the presence of a catalytic amount of ZnI2 to give the corresponding trans-4-heterofunction-substituted azetidin-2-ones in high yields.

A NOVEL SUBSTITUTION REACTION OF 4-SULFINYLAZETIDIN-2-ONE WITH SILYLATED HETERONUCLEOPHILES: AN EFFICIENT SYNTHESIS OF 4-HETEROFUNCTION SUBSTITUTED 3-(1-HYDROXY)ETHYLAZETIDIN-2-ONES

4-Sulfinylazetidin-2-one was reacted with silylated heteronucleophiles in the presence of a catalytic amount of zinc iodide to give the corresponding trans-4-heterofunction substituted azetidin-2-ones in high yields.