109715-77-7

Basic information

• Product Name: (3S,4R)-3-<(R)-1-(t-Butyldimethylsilyloxy)ethyl>-4-<(R)-1-((S)-4-benzyl-2-oxazolidone-3-carbonyl)ethyl>-2-azetidinone
• Synonyms: (3S,4R)-3-<(R)-1-(t-Butyldimethylsilyloxy)ethyl>-4-<(R)-1-((S)-4-benzyl-2-oxazolidone-3-carbonyl)ethyl>-2-azetidinone
• CAS NO: 109715-77-7
• Molecular Weight: 460.646
• Mol File: 109715-77-7.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (3S,4R)-3-<(R)-1-(t-Butyldimethylsilyloxy)ethyl>-4-<(R)-1-((S)-4-benzyl-2-oxazolidone-3-carbonyl)ethyl>-2-azetidinone(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,4R)-3-<(R)-1-(t-Butyldimethylsilyloxy)ethyl>-4-<(R)-1-((S)-4-benzyl-2-oxazolidone-3-carbonyl)ethyl>-2-azetidinone(109715-77-7)
• EPA Substance Registry System: (3S,4R)-3-<(R)-1-(t-Butyldimethylsilyloxy)ethyl>-4-<(R)-1-((S)-4-benzyl-2-oxazolidone-3-carbonyl)ethyl>-2-azetidinone(109715-77-7)

Safety Data

• Hazardous Substances Data: 109715-77-7(Hazardous Substances Data)

Upstream product

• 3182-95-4 L-Phenylalaninol 
• 76899-07-5 (3R,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one 
• 131685-53-5 (S)-4-benzyl-3-propionyl-2-oxazolidinone 
• 90719-32-7 (S)-4-Benzyl-2-oxazolidinone 
• 192864-91-8 (4S)-4-benzyl-3-(2-bromopropanoyl)-1,3-oxazolidin-2-one 

Downstream Products

• 93711-85-4 (2R)-2-[(2S,3S)-3-{(1R)-1-(t-butyldimethylsilyloxy)ethyl}-4-oxoazetidin-2-yl]propionic acid 
• 139976-61-7 7-<1-<1-<(tert-butyldimethylsilyl)oxy>ethyl>>-6-methyl-9a-carbobenzoxy-1,8-dioxoazetidino<1,2-c>perhydropyrrolo<1,2-a>pyrimidine 
• 139976-62-8 7-<1-<1-<(tert-butyldimethylsilyl)oxy>ethyl>>-1-hydroxy-6-methyl-9a-carbobenzoxy-8-oxoazetidino<1,2-c>perhydropyrrolo<1,2-a>pyrimidine 
• 139976-63-9 7-<1-(1-hydroxyethyl)>-1-hydroxy-6-methyl-9a-carbobenzoxy-8-oxoazetidino<1,2-c>perhydropyrrolo<1,2-a>pyrimidine 
• 96035-98-2 (3S,4S)-4-<(1R)-1-benzyloxycarbonylethyl>-3-<(1R)-1-tert-butyldimethylsilyloxyethyl>-2-azetidinone 

Relevant articles and documents

Highly stereocontrolled synthesis of the 1β-methylcarbapenem key intermediate by the Reformatsky reaction of 3-(2-bromopropionyl)-2-oxazolidone derivatives with a 4-acetoxy-2-azetidinone

The key synthetic intermediate (4) of 1β-methylcarbapenems (1~3) was efficiently synthesized by employing highly stereocontrolled Reformatsky reaction (C4-alkylation) of 3-(2-bromopropionyl)-2-oxazolidone derivatives (6) with (3R,4R)-4-acetoxy-3-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-2-azetidino ne (5) in the presence of zinc dust followed by removal of 2-oxazolidone moieties. The best diastereoselectivity (β:α = 95:5) could be realized by uses of sterically crowded achiral 2-oxazolidone derivatives such as 4,4-dimethyl-, 4,4,5,5-tetramethyl, and 4,4-dibutyl-5,5-pentamethylene-2-oxazolidone and higher reaction temperatures (refluxing tetrahydrofran). The remarkable diastereoselectivities observed for the Reformatsky reactions could be explained by means of the weakly chelating transition state models.

Method for manufacturing stereoselective preparation of 4-bma using a chiral auxiliary and chiral auxiliary

The present invention relates to a process for preparing (3R,4S)-3-[[[R]-1 ' -t-butyldimethylsilyloxy ]ethyl]-4-[(R)-1 "-carboxyethyl]-2-azetidinone (beta- methylazetidin-2-one; 4-BMA), a key intermediate for the synthesis of carbapenem and penem antibiotics. Specifically, the present invention relates to a process comprising first, the preparation of a chiral auxiliary from cheap L-Phenylalaninol, and then the preparation of 4-BMA in high yield and high selectivity, under industrially mild condition.

A highly stereoselective synthesis of a key intermediate of 1β-methylcarbapenems employing the Reformatsky reaction of 3-(2-bromopropionyl)-2-oxazolidone derivatives

-